2034:
1995:
1954:
384:
223:
1254:
37:
1247:
631:
641:
636:
824:
1403:
52:
828:
2542:
28:
947:
870:
829:
827:
1670:
649:
2479:
Vitaku, E.; D. T. Smith; J. T. Njardarson (2014). "Analysis of the
Structural Diversity, Substitution Patterns, and Frequency of Nitrogen Heterocycles among U.S. FDA Approved Pharmaceuticals".
611:
845:
1215:, and the other in an equatorial position. After much controversy during the 1950s–1970s, the equatorial conformation was found to be more stable by 0.72 kcal/mol in the gas phase. In
1219:, a range between 0.2 and 0.6 kcal/mol has been estimated, but in polar solvents the axial conformer may be more stable. The two conformers interconvert rapidly through
755:
830:
1840:
1835:[Collegiate Board Resolution No. 784 - Lists of Narcotic, Psychotropic, Precursor, and Other Substances under Special Control] (in Brazilian Portuguese).
1134:
1124:
747:
2308:
Carballeira, Luis; Pérez Juste, Ignacio (1998). "Influence of calculation level and effect of methylation on axial/equatorial equilibria in piperidines".
1390:
A significant industrial application of piperidine is for the production of dipiperidinyl dithiuram tetrasulfide, which is used as an accelerator of the
1413:
Piperidine and its derivatives are ubiquitous building blocks in pharmaceuticals and fine chemicals. The piperidine structure is found in, for example:
2577:
2515:"List of Precursors and Chemicals Frequently Used in the Illicit Manufacture of Narcotic Drugs and Psychotropic Substances Under International Control"
960:
892:
2052:
2343:
Blackburne, Ian D.; Katritzky, Alan R.; Yoshito
Takeuchi (1975). "Conformation of piperidine and of derivatives with additional ring hetero atoms".
1744:
925:
852:
1023:. Although piperidine is a common organic compound, it is best known as a representative structure element within many pharmaceuticals and
440:
1907:
Pianaro, Adriana; Fox, Eduardo G.P.; Bueno, Odair C.; Marsaioli, Anita J. (May 2012). "Rapid configuration analysis of the solenopsins".
929:
2321:
1693:
751:
1424:
1505:
1235:-methylpiperidine, the equatorial conformation is preferred by 3.16 kcal/mol, which is much larger than the preference in
2434:
1891:
1728:
259:
695:
1832:
1935:
2069:
1828:
955:
398:
2514:
838:
2572:
967:
877:
2008:
1044:
1630:
1833:"RDC Nº 784 - Listas de Substâncias Entorpecentes, Psicotrópicas, Precursoras e Outras sob Controle Especial"
1372:
1009:–) and one amine bridge (–NH–). It is a colorless liquid with an odor described as objectionable, typical of
1836:
689:
331:
218:
1211:. Unlike cyclohexane, piperidine has two distinguishable chair conformations: one with the N–H bond in an
2546:
1227:
for this process, estimated at 6.1 kcal/mol, is substantially lower than the 10.4 kcal/mol for
362:
2223:
735:
180:
1712:
561:
1971:
1967:
1040:
230:
2033:
1994:
1953:
1709:
Nomenclature of
Organic Chemistry : IUPAC Recommendations and Preferred Names 2013 (Blue Book)
1284:
791:
379:
2243:), is a naturally occurring inhibitor of phosphatidylinositol-3-kinase signaling and angiogenesis"
1212:
2567:
2450:
Claxton, George P.; Allen, Lloyd; Grisar, J. Martin (1977). "2,3,4,5-Tetrahydropyridine Trimer".
580:
2012:
630:
1868:
1671:
United
Nations Convention Against Illicit Traffic in Narcotic Drugs and Psychotropic Substances
1642:
Piperidine is also commonly used in chemical degradation reactions, such as the sequencing of
635:
2210:
1483:
1368:
1327:
995:
707:
663:
623:
64:
2562:
2028:(The new alkali derived from piperine, which I will designate by the name of 'piperidine',…
1767:
1391:
1291:
1067:
640:
340:
140:
74:
767:
739:
200:
8:
1603:
1311:
116:
106:
2050:
Eller, Karsten; Henkes, Erhard; Rossbacher, Roland; Höke, Hartmut. "Amines, Aliphatic".
1771:
383:
222:
160:
2325:
2267:
2238:
2026:
L'alcali nouveau dérivé de la pipérine, que je désignerai sous le nom de 'pipéridine',…
1783:
1738:
1361:
1295:
1224:
1220:
1204:
715:
2496:
2452:
2430:
2403:
2272:
2065:
1887:
1862:
1724:
1663:
1236:
864:
2329:
1787:
1758:
Amoore, J. E. (1975). "Specific anosmia to 1-pyrroline: The spermous primary odor".
779:
2488:
2461:
2379:
2352:
2317:
2262:
2254:
2179:
2148:
2121:
2112:
Späth; Englaender (1935). "Über das
Vorkommen von Piperidin im schwarzen Pfeffer".
2094:
2057:
1983:
1916:
1810:
1775:
1716:
1651:
1620:
1357:
1253:
1216:
1171:
1002:
983:
759:
550:
463:
36:
2183:
2258:
1920:
1617:
1491:
1462:
1447:
1384:
1380:
1180:
1099:
304:
2398:
1972:"Vorläufiger Bericht über die Wirkung der Salpetersäure auf organische Alkalien"
1720:
703:
1452:
1376:
1228:
1188:
938:
795:
723:
1974:[Preliminary report on the effect of nitric acid on organic alkalis].
1246:
719:
2556:
2465:
2152:
2125:
2098:
2061:
1987:
1674:
1609:
1530:
1323:
1059:
1015:
731:
539:
529:
211:
2500:
2276:
1561:
1551:
1150:
1119:
1020:
598:
851:
787:
2521:
2370:
Anet, F. A. L.; Yavari, Issa (1977). "Nitrogen inversion in piperidine".
2322:
10.1002/(SICI)1096-987X(199806)19:8<961::AID-JCC14>3.0.CO;2-A
1647:
1556:
1541:
1518:
1208:
1153:
its spicy taste. This gave the compound its name. Other examples are the
1052:
917:
771:
2427:
March's
Advanced Organic Chemistry: Reactions, Mechanisms, and Structure
2383:
2356:
1814:
1673:
due to its use (peaking in the 1970s) in the clandestine manufacture of
837:
775:
743:
2139:
Pictet, Amé; Pictet, René (1927). "Sur l'alcaloïde volatil du poivre".
1779:
1659:
1585:
1574:
1536:
1511:
1497:
1476:
1437:
1430:
1336:
1299:
1158:
1028:
921:
844:
763:
488:
249:
231:
191:
2492:
1402:
783:
2478:
1590:
1546:
1523:
1457:
1441:
1406:
1166:
1129:
677:
592:
351:
937:
Except where otherwise noted, data are given for materials in their
51:
2342:
1801:
Hall, H. K. (1957). "Correlation of the Base
Strengths of Amines".
1579:
1417:
1192:
1176:
1162:
1154:
1146:
1142:
1113:
1063:
1048:
1024:
913:
810:
279:
1371:
with better hydrocarbon solubility than other amide solvents, and
803:
139:
1596:
1353:
1280:
1184:
1107:
727:
519:
291:
2015:[Investigations of a new alkali derived from piperine].
669:
2541:
1625:
1568:
1276:
1141:
The piperidine structural motif is present in numerous natural
1103:
171:
1039:
Piperidine was first reported in 1850 by the
Scottish chemist
1047:, who named it. Both of them obtained piperidine by reacting
1010:
998:
315:
151:
129:
1409:
is a piperidine derivative widely used to prevent hair loss.
699:
367:
27:
2085:
Marvel, C. S.; Lazier, W. A. (1929). "Benzoyl
Piperidine".
1655:
509:
270:
1098:
Pyridine can also be reduced to piperidine via a modified
711:
1643:
1283:. Enamines derived from piperidine are substrates in the
2237:
Arbiser, J. L.; Kau, T.; Konar, M.; et al. (2007).
1906:
1043:
and again, independently, in 1852 by the French chemist
673:
2520:. International Narcotics Control Board. Archived from
2239:"Solenopsin, the alkaloidal component of the fire ant (
2013:"Recherches sur un nouvel alcali dérivé de la pipérine"
1669:
Piperidine is listed as a Table II precursor under the
2307:
2289:
2049:
1860:
1650:. Piperidine is also commonly used as a base for the
2196:
258:
2449:
1397:
2554:
1114:Natural occurrence of piperidine and derivatives
1001:consists of a six-membered ring containing five
303:
2236:
2111:
826:
115:
2397:Kane, Vinayak V.; Jones, Maitland Jr. (1990).
2053:Ullmann's Encyclopedia of Industrial Chemistry
799:
681:
2138:
2084:
1743:: CS1 maint: DOI inactive as of June 2024 (
1360:. The same is true for certain derivatives:
1058:Industrially, piperidine is produced by the
2424:
2399:"Spiro[5.7]trideca-1,4-dien-3-one"
2369:
2045:
2043:
1936:"When piperidine was a structural problem"
382:
221:
199:
2578:Substances discovered in the 19th century
2396:
2266:
2165:
1694:"International Chemical Safety Card 0317"
1473:) receptor antagonists/inverse agonists:
1118:Piperidine itself has been obtained from
339:
2425:Smith, Michael B.; March, Jerry (2001).
2303:
2301:
1966:
1933:
1700:
1401:
1310:NCl. The resulting chloramine undergoes
407:InChI=1S/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
2040:
2007:
1884:Elsevier's Dictionary of Chemoetymology
1881:
1646:in the cleavage of particular modified
1425:selective serotonin reuptake inhibitors
1317:
424:InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
417:InChI=1/C5H11N/c1-2-4-6-5-3-1/h6H,1-5H2
378:
2555:
2294:(4th ed.). The Blakiston Company.
1827:
1757:
1506:selective estrogen receptor modulators
544:106 °C (223 °F; 379 K)
514:Semen-like, fishy-ammoniacal, pungent
212:
2298:
2230:
1943:Bulletin for the History of Chemistry
1275:Piperidine is widely used to convert
1013:. The name comes from the genus name
410:Key: NQRYJNQNLNOLGT-UHFFFAOYSA-N
179:
159:
2429:(5th ed.). Wiley-Interscience.
1800:
534:−7 °C (19 °F; 266 K)
427:Key: NQRYJNQNLNOLGT-UHFFFAOYAY
294:
278:
13:
2310:Journal of Computational Chemistry
822:
35:
26:
14:
2589:
2534:
2540:
2172:South African Journal of Science
2032:
1993:
1976:Annalen der Chemie und Pharmacie
1952:
1379:base, useful because of its low
1252:
1245:
945:
639:
634:
629:
481:
475:
50:
2507:
2472:
2443:
2418:
2390:
2363:
2336:
2283:
2197:Juraschewski; Stepanov (1939).
2190:
2159:
2132:
2105:
2078:
2001:
1960:
1843:from the original on 2023-08-03
1198:
941:(at 25 °C , 100 kPa).
2481:Journal of Medicinal Chemistry
2290:Thomas Anderson Henry (1949).
1927:
1900:
1875:
1861:Frank Johnson Welcher (1947).
1854:
1821:
1794:
1751:
1713:The Royal Society of Chemistry
1686:
1398:List of piperidine medications
1019:, which is the Latin word for
986:with the molecular formula (CH
886:
469:
1:
1680:
1634:-Methyl-3-piperidyl benzilate
1373:2,2,6,6-tetramethylpiperidine
1034:
2259:10.1182/blood-2006-06-029934
2170:N.E.Br. as a stock poison".
1921:10.1016/j.tetasy.2012.05.005
1314:to afford the cyclic imine.
1270:
1027:, such as natural-occurring
7:
2166:Rimington, Claude (1934). "
1934:Warnhoff, Edgar W. (1998).
1882:Senning, Alexander (2006).
1867:. D. Van Nostrand. p.
1864:Organic Analytical Reagents
1721:10.1039/9781849733069-FP001
22:
10:
2594:
2413:, vol. 7, p. 473
1294:, piperidine converts to
1183:, and the toxic alkaloid
935:
902:
610:
605:
456:
436:
394:
99:
85:
73:
63:
58:
49:
21:
2466:10.15227/orgsyn.056.0118
2153:10.1002/hlca.19270100175
2126:10.1002/cber.19350681211
2099:10.15227/orgsyn.009.0016
2062:10.1002/14356007.a02_001
1988:10.1002/jlac.18500750110
1839:(published 2023-04-04).
1352:Piperidine is used as a
1285:Stork enamine alkylation
1264:equatorial conformation
1191:, which was used to put
690:Precautionary statements
2573:Foul-smelling chemicals
2056:. Weinheim: Wiley-VCH.
1886:. Amsterdam: Elsevier.
1837:Diário Oficial da União
1723:(inactive 2024-06-30).
1383:and high solubility in
1347:
1343:, ppm) 2.79, 2.19, 1.51
581:Magnetic susceptibility
2184:10520/AJA00382353_6425
2141:Helvetica Chimica Acta
1909:Tetrahedron: Asymmetry
1410:
1239:, 1.74 kcal/mol.
833:
40:
31:
1715:. 2014. p. 142.
1405:
1369:polar aprotic solvent
1333:, ppm) 47, 27.2, 25.2
1203:Piperidine prefers a
1135:Petrosimonia monandra
832:
39:
30:
2549:at Wikimedia Commons
2168:Psilocaulon absimile
1662:used in solid-phase
1604:Arylcyclohexylamines
1392:sulfur vulcanization
1318:NMR chemical control
1292:calcium hypochlorite
1290:Upon treatment with
1125:Psilocaulon absimile
1068:molybdenum disulfide
815:(fire diamond)
75:Preferred IUPAC name
2487:(24): 10257–10274.
2384:10.1021/ja00450a064
2357:10.1021/ar50093a003
2292:The Plant Alkaloids
1815:10.1021/ja01577a030
1772:1975JCEco...1..299A
1377:sterically hindered
1312:dehydrohalogenation
574:11.22 (protonated)
551:Solubility in water
496: g·mol
92:Pentamethyleneamine
18:
2241:Solenopsis invicta
2199:J. Gen. Chem. USSR
2114:Chemische Berichte
1780:10.1007/BF00988831
1696:. 28 January 2024.
1420:(Insect repellent)
1411:
1302:with the formula C
1296:N-chloropiperidine
1261:axial conformation
1225:activation barrier
1223:; the free energy
1221:nitrogen inversion
1205:chair conformation
968:Infobox references
903:Related compounds
834:
41:
32:
16:
2545:Media related to
2493:10.1021/jm501100b
2453:Organic Syntheses
2436:978-0-471-58589-3
2411:Collected Volumes
2404:Organic Syntheses
2218:Missing or empty
2120:(12): 2218–2221.
1893:978-0-444-52239-9
1809:(20): 5441–5444.
1730:978-0-85404-182-4
1664:peptide synthesis
1365:-formylpiperidine
1268:
1267:
1237:methylcyclohexane
1231:. In the case of
1217:nonpolar solvents
1169:of tree tobacco (
1066:, usually over a
1003:methylene bridges
976:Chemical compound
974:
973:
909:Related compounds
895:(Drug precursors)
890:
865:Safety data sheet
664:Hazard statements
504:Colorless liquid
363:CompTox Dashboard
141:Interactive image
88:Hexahydropyridine
45:
44:
2585:
2544:
2529:
2528:
2526:
2519:
2511:
2505:
2504:
2476:
2470:
2468:
2447:
2441:
2440:
2422:
2416:
2414:
2407:
2394:
2388:
2387:
2378:(8): 2794–2796.
2372:J. Am. Chem. Soc
2367:
2361:
2360:
2340:
2334:
2333:
2305:
2296:
2295:
2287:
2281:
2280:
2270:
2234:
2228:
2227:
2221:
2216:
2214:
2206:
2194:
2188:
2187:
2163:
2157:
2156:
2136:
2130:
2129:
2109:
2103:
2102:
2082:
2076:
2075:
2047:
2038:
2037:
2036:
2030:
2009:Cahours, Auguste
2005:
1999:
1998:
1997:
1991:
1968:Anderson, Thomas
1964:
1958:
1957:
1956:
1950:
1940:
1931:
1925:
1924:
1904:
1898:
1897:
1879:
1873:
1872:
1858:
1852:
1851:
1849:
1848:
1825:
1819:
1818:
1803:J. Am. Chem. Soc
1798:
1792:
1791:
1755:
1749:
1748:
1742:
1734:
1707:"Front Matter".
1704:
1698:
1697:
1690:
1621:chemical weapons
1492:inverse agonists
1385:organic solvents
1256:
1249:
1242:
1241:
1172:Nicotiana glauca
1145:. These include
984:organic compound
958:
952:
949:
948:
888:
885:
854:
847:
840:
825:
805:
801:
797:
793:
789:
785:
781:
777:
773:
769:
765:
761:
757:
753:
749:
745:
741:
737:
733:
729:
725:
721:
717:
713:
709:
705:
701:
697:
683:
679:
675:
671:
643:
638:
633:
587:-64.2·10 cm/mol
495:
483:
477:
471:
464:Chemical formula
387:
386:
371:
369:
343:
307:
296:
282:
262:
233:
225:
214:
203:
183:
163:
143:
119:
54:
23:
19:
15:
2593:
2592:
2588:
2587:
2586:
2584:
2583:
2582:
2553:
2552:
2537:
2532:
2524:
2517:
2513:
2512:
2508:
2477:
2473:
2448:
2444:
2437:
2423:
2419:
2409:
2395:
2391:
2368:
2364:
2341:
2337:
2306:
2299:
2288:
2284:
2235:
2231:
2219:
2217:
2208:
2207:
2195:
2191:
2164:
2160:
2137:
2133:
2110:
2106:
2083:
2079:
2072:
2048:
2041:
2031:
2006:
2002:
1992:
1965:
1961:
1951:
1938:
1932:
1928:
1905:
1901:
1894:
1880:
1876:
1859:
1855:
1846:
1844:
1826:
1822:
1799:
1795:
1756:
1752:
1736:
1735:
1731:
1706:
1705:
1701:
1692:
1691:
1687:
1683:
1618:anticholinergic
1487:
1472:
1463:Desoxypipradrol
1448:Methylphenidate
1400:
1381:nucleophilicity
1350:
1342:
1331:
1320:
1309:
1305:
1273:
1201:
1116:
1100:Birch reduction
1093:
1089:
1085:
1081:
1077:
1045:Auguste Cahours
1041:Thomas Anderson
1037:
1008:
993:
989:
977:
970:
965:
964:
963: ?)
954:
950:
946:
942:
928:
924:
920:
916:
910:
898:
859:
858:
857:
856:
849:
842:
835:
831:
823:
692:
666:
652:
626:
584:
570:
553:
493:
480:
474:
466:
452:
449:
444:
443:
432:
429:
428:
425:
419:
418:
412:
411:
408:
402:
401:
390:
372:
365:
346:
326:
310:
297:
285:
265:
252:
243:
206:
186:
166:
146:
133:
122:
109:
95:
93:
91:
89:
81:
80:
69:
12:
11:
5:
2591:
2581:
2580:
2575:
2570:
2568:Amine solvents
2565:
2551:
2550:
2536:
2535:External links
2533:
2531:
2530:
2527:on 2008-02-27.
2506:
2471:
2442:
2435:
2417:
2389:
2362:
2351:(9): 300–306.
2345:Acc. Chem. Res
2335:
2316:(8): 961–976.
2297:
2282:
2229:
2189:
2158:
2131:
2104:
2077:
2071:978-3527306732
2070:
2039:
2017:Comptes Rendus
2000:
1959:
1926:
1915:(9): 635–642.
1899:
1892:
1874:
1853:
1831:(2023-03-31).
1820:
1793:
1766:(3): 299–310.
1750:
1729:
1699:
1684:
1682:
1679:
1640:
1639:
1638:
1637:
1628:
1615:
1614:
1613:
1601:
1600:
1599:
1594:
1588:
1583:
1577:
1566:
1565:
1564:
1559:
1554:
1549:
1544:
1539:
1528:
1527:
1526:
1516:
1515:
1514:
1502:
1501:
1500:
1485:
1484:Histamine 3 (H
1481:
1480:
1479:
1470:
1469:Histamine 1 (H
1467:
1466:
1465:
1460:
1455:
1453:Ethylphenidate
1450:
1435:
1434:
1433:
1421:
1399:
1396:
1349:
1346:
1345:
1344:
1340:
1334:
1329:
1319:
1316:
1307:
1303:
1272:
1269:
1266:
1265:
1262:
1258:
1257:
1250:
1229:ring inversion
1213:axial position
1200:
1197:
1189:poison hemlock
1181:Indian tobacco
1149:, which gives
1115:
1112:
1096:
1095:
1091:
1087:
1083:
1079:
1075:
1036:
1033:
1006:
991:
987:
975:
972:
971:
966:
944:
943:
939:standard state
936:
933:
932:
911:
908:
905:
904:
900:
899:
897:
896:
882:
880:
874:
873:
868:
861:
860:
850:
843:
836:
821:
820:
819:
818:
816:
807:
806:
756:P305+P351+P338
748:P303+P361+P353
740:P301+P330+P331
693:
688:
685:
684:
667:
662:
659:
658:
653:
648:
645:
644:
627:
622:
619:
618:
608:
607:
603:
602:
601:at 25 °C
595:
589:
588:
585:
579:
576:
575:
572:
568:
558:
557:
554:
549:
546:
545:
542:
536:
535:
532:
526:
525:
522:
516:
515:
512:
506:
505:
502:
498:
497:
491:
485:
484:
478:
472:
467:
462:
459:
458:
454:
453:
451:
450:
447:
439:
438:
437:
434:
433:
431:
430:
426:
423:
422:
420:
416:
415:
413:
409:
406:
405:
397:
396:
395:
392:
391:
389:
388:
375:
373:
361:
358:
357:
354:
348:
347:
345:
344:
336:
334:
328:
327:
325:
324:
320:
318:
312:
311:
309:
308:
300:
298:
290:
287:
286:
284:
283:
275:
273:
267:
266:
264:
263:
255:
253:
248:
245:
244:
242:
241:
237:
235:
227:
226:
216:
208:
207:
205:
204:
196:
194:
188:
187:
185:
184:
176:
174:
168:
167:
165:
164:
156:
154:
148:
147:
145:
144:
136:
134:
127:
124:
123:
121:
120:
112:
110:
105:
102:
101:
97:
96:
90:Azacyclohexane
87:
83:
82:
78:
77:
71:
70:
67:
61:
60:
56:
55:
47:
46:
43:
42:
33:
9:
6:
4:
3:
2:
2590:
2579:
2576:
2574:
2571:
2569:
2566:
2564:
2561:
2560:
2558:
2548:
2543:
2539:
2538:
2523:
2516:
2510:
2502:
2498:
2494:
2490:
2486:
2482:
2475:
2467:
2463:
2459:
2455:
2454:
2446:
2438:
2432:
2428:
2421:
2412:
2406:
2405:
2400:
2393:
2385:
2381:
2377:
2373:
2366:
2358:
2354:
2350:
2346:
2339:
2331:
2327:
2323:
2319:
2315:
2311:
2304:
2302:
2293:
2286:
2278:
2274:
2269:
2264:
2260:
2256:
2252:
2248:
2244:
2242:
2233:
2225:
2212:
2204:
2200:
2193:
2185:
2181:
2177:
2173:
2169:
2162:
2154:
2150:
2146:
2142:
2135:
2127:
2123:
2119:
2115:
2108:
2100:
2096:
2092:
2088:
2081:
2073:
2067:
2063:
2059:
2055:
2054:
2046:
2044:
2035:
2029:
2027:
2022:
2018:
2014:
2010:
2004:
1996:
1989:
1985:
1981:
1977:
1973:
1969:
1963:
1955:
1948:
1944:
1937:
1930:
1922:
1918:
1914:
1910:
1903:
1895:
1889:
1885:
1878:
1870:
1866:
1865:
1857:
1842:
1838:
1834:
1830:
1824:
1816:
1812:
1808:
1804:
1797:
1789:
1785:
1781:
1777:
1773:
1769:
1765:
1761:
1760:J. Chem. Ecol
1754:
1746:
1740:
1732:
1726:
1722:
1718:
1714:
1711:. Cambridge:
1710:
1703:
1695:
1689:
1685:
1678:
1676:
1675:phencyclidine
1672:
1667:
1665:
1661:
1657:
1653:
1649:
1645:
1635:
1633:
1629:
1627:
1624:
1623:
1622:
1619:
1616:
1611:
1608:
1607:
1605:
1602:
1598:
1595:
1592:
1589:
1587:
1584:
1581:
1578:
1576:
1573:
1572:
1570:
1567:
1563:
1560:
1558:
1555:
1553:
1550:
1548:
1545:
1543:
1540:
1538:
1535:
1534:
1533:medications:
1532:
1531:Antipsychotic
1529:
1525:
1522:
1521:
1520:
1517:
1513:
1510:
1509:
1507:
1503:
1499:
1496:
1495:
1493:
1489:
1482:
1478:
1475:
1474:
1468:
1464:
1461:
1459:
1456:
1454:
1451:
1449:
1446:
1445:
1443:
1439:
1436:
1432:
1429:
1428:
1426:
1422:
1419:
1416:
1415:
1414:
1408:
1404:
1395:
1393:
1388:
1386:
1382:
1378:
1374:
1370:
1366:
1364:
1359:
1355:
1338:
1335:
1332:
1325:
1322:
1321:
1315:
1313:
1301:
1297:
1293:
1288:
1286:
1282:
1278:
1263:
1260:
1259:
1255:
1251:
1248:
1244:
1243:
1240:
1238:
1234:
1230:
1226:
1222:
1218:
1214:
1210:
1207:, similar to
1206:
1196:
1194:
1190:
1186:
1182:
1178:
1174:
1173:
1168:
1164:
1160:
1156:
1152:
1148:
1144:
1139:
1137:
1136:
1131:
1127:
1126:
1121:
1111:
1109:
1105:
1101:
1073:
1072:
1071:
1069:
1065:
1061:
1060:hydrogenation
1056:
1054:
1050:
1046:
1042:
1032:
1030:
1026:
1022:
1018:
1017:
1012:
1004:
1000:
997:
985:
981:
969:
962:
957:
940:
934:
931:
927:
926:Phosphorinane
923:
919:
915:
912:
907:
906:
901:
894:
884:
883:
881:
879:
876:
875:
872:
869:
866:
863:
862:
855:
848:
841:
817:
814:
813:
809:
808:
694:
691:
687:
686:
668:
665:
661:
660:
657:
654:
651:
647:
646:
642:
637:
632:
628:
625:
621:
620:
616:
614:
609:
604:
600:
596:
594:
591:
590:
586:
582:
578:
577:
573:
567:
563:
560:
559:
555:
552:
548:
547:
543:
541:
540:Boiling point
538:
537:
533:
531:
530:Melting point
528:
527:
523:
521:
518:
517:
513:
511:
508:
507:
503:
500:
499:
492:
490:
487:
486:
468:
465:
461:
460:
455:
446:
445:
442:
435:
421:
414:
404:
403:
400:
393:
385:
381:
380:DTXSID6021165
377:
376:
374:
364:
360:
359:
355:
353:
350:
349:
342:
338:
337:
335:
333:
330:
329:
322:
321:
319:
317:
314:
313:
306:
302:
301:
299:
293:
289:
288:
281:
277:
276:
274:
272:
269:
268:
261:
257:
256:
254:
251:
247:
246:
239:
238:
236:
234:
229:
228:
224:
220:
217:
215:
213:ECHA InfoCard
210:
209:
202:
198:
197:
195:
193:
190:
189:
182:
178:
177:
175:
173:
170:
169:
162:
158:
157:
155:
153:
150:
149:
142:
138:
137:
135:
131:
126:
125:
118:
114:
113:
111:
108:
104:
103:
98:
84:
76:
72:
66:
62:
57:
53:
48:
38:
34:
29:
25:
24:
20:
2522:the original
2509:
2484:
2480:
2474:
2457:
2451:
2445:
2426:
2420:
2410:
2402:
2392:
2375:
2371:
2365:
2348:
2344:
2338:
2313:
2309:
2291:
2285:
2253:(2): 560–5.
2250:
2246:
2240:
2232:
2220:|title=
2211:cite journal
2202:
2198:
2192:
2175:
2171:
2167:
2161:
2144:
2140:
2134:
2117:
2113:
2107:
2090:
2086:
2080:
2051:
2025:
2024:
2020:
2016:
2003:
1979:
1975:
1962:
1946:
1942:
1929:
1912:
1908:
1902:
1883:
1877:
1863:
1856:
1845:. Retrieved
1823:
1806:
1802:
1796:
1763:
1759:
1753:
1708:
1702:
1688:
1668:
1652:deprotection
1641:
1636:(JB-336, BZ)
1631:
1593:(meperidine)
1562:Thioridazine
1552:Mesoridazine
1519:Vasodilators
1490:antagonists/
1412:
1389:
1375:is a highly
1362:
1351:
1289:
1274:
1232:
1202:
1199:Conformation
1170:
1151:black pepper
1140:
1133:
1123:
1120:black pepper
1117:
1097:
1082:N + 3 H
1057:
1038:
1014:
996:heterocyclic
979:
978:
878:Legal status
811:
655:
612:
565:
316:RTECS number
100:Identifiers
86:Other names
2563:Piperidines
2178:: 184–193.
2147:: 593–595.
2023:: 481–484.
1660:amino acids
1648:nucleotides
1612:and analogs
1582:and analogs
1557:Risperidone
1542:Haloperidol
1394:of rubber.
1209:cyclohexane
1053:nitric acid
1029:solenopsins
918:Pyrrolidine
650:Signal word
524:0.862 g/mL
501:Appearance
457:Properties
219:100.003.467
181:ChEMBL15487
161:CHEBI:18049
17:Piperidine
2557:Categories
2547:Piperidine
2087:Org. Synth
1847:2023-08-15
1681:References
1586:Loperamide
1575:Dipipanone
1537:Droperidol
1512:Raloxifene
1498:Pitolisant
1488:) receptor
1477:Loratadine
1442:nootropics
1438:Stimulants
1431:Paroxetine
1300:chloramine
1287:reaction.
1195:to death.
1159:solenopsin
1132:), and in
1070:catalyst:
1035:Production
980:Piperidine
922:Piperazine
624:Pictograms
489:Molar mass
341:67I85E138Y
250:IUPHAR/BPS
192:ChemSpider
128:3D model (
107:CAS Number
79:Piperidine
68:Piperidine
65:IUPAC name
1982:: 80–83.
1739:cite book
1591:Pethidine
1547:Melperone
1524:Minoxidil
1458:Pipradrol
1407:Minoxidil
1356:and as a
1271:Reactions
1167:anabasine
1143:alkaloids
1130:Aizoaceae
1025:alkaloids
994:NH. This
796:P403+P235
792:P403+P233
788:P370+P378
752:P304+P340
744:P302+P352
615:labelling
593:Viscosity
556:Miscible
352:UN number
323:TM3500000
240:203-813-0
232:EC Number
2501:25255204
2330:98028598
2277:16990598
2011:(1852).
1970:(1850).
1949:: 29–34.
1841:Archived
1788:19318345
1580:Fentanyl
1418:Icaridin
1281:enamines
1193:Socrates
1177:lobeline
1163:nicotine
1155:fire ant
1147:piperine
1064:pyridine
1049:piperine
930:Arsinane
914:Pyridine
893:Class D1
812:NFPA 704
606:Hazards
583:(χ)
448:C1CCNCC1
117:110-89-4
2460:: 118.
2268:1785094
2205:: 1687.
1768:Bibcode
1597:Prodine
1569:Opioids
1423:SSRIs (
1354:solvent
1339:: (CDCl
1277:ketones
1185:coniine
1165:analog
1122:, from
1108:ethanol
961:what is
959: (
562:Acidity
520:Density
292:PubChem
94:Azinane
2499:
2433:
2328:
2275:
2265:
2093:: 16.
2068:
1890:
1829:Anvisa
1786:
1727:
1626:Ditran
1504:SERM (
1161:, the
1157:toxin
1104:sodium
1102:using
1021:pepper
1011:amines
982:is an
956:verify
953:
891:
867:(SDS)
656:Danger
597:1.573
494:85.150
441:SMILES
280:C01746
172:ChEMBL
59:Names
2525:(PDF)
2518:(PDF)
2326:S2CID
2247:Blood
1939:(PDF)
1784:S2CID
1367:is a
1337:H NMR
1324:C NMR
1187:from
1051:with
1016:Piper
999:amine
871:MSDS1
399:InChI
356:2401
152:ChEBI
130:JSmol
2497:PMID
2431:ISBN
2273:PMID
2224:help
2066:ISBN
1888:ISBN
1745:link
1725:ISBN
1656:Fmoc
1440:and
1358:base
1348:Uses
1328:CDCl
1298:, a
1005:(–CH
804:P501
800:P405
784:P363
780:P361
776:P322
772:P321
768:P312
764:P311
760:P310
736:P280
732:P271
728:P264
724:P261
720:P260
716:P243
712:P242
708:P241
704:P240
700:P233
696:P210
682:H331
678:H314
674:H311
670:H225
510:Odor
332:UNII
305:8082
271:KEGG
260:5477
201:7791
2489:doi
2462:doi
2380:doi
2353:doi
2318:doi
2263:PMC
2255:doi
2251:109
2180:hdl
2149:doi
2122:doi
2095:doi
2058:doi
1984:doi
1917:doi
1869:149
1811:doi
1776:doi
1717:doi
1654:of
1644:DNA
1610:PCP
1326:: (
1279:to
1179:of
1175:),
1106:in
1086:→ C
1062:of
613:GHS
368:EPA
295:CID
2559::
2495:.
2485:57
2483:.
2458:56
2456:.
2408:;
2401:.
2376:99
2374:.
2347:.
2324:.
2314:19
2312:.
2300:^
2271:.
2261:.
2249:.
2245:.
2215::
2213:}}
2209:{{
2201:.
2176:31
2174:.
2145:10
2143:.
2118:68
2116:.
2089:.
2064:.
2042:^
2021:34
2019:.
1980:75
1978:.
1947:22
1945:.
1941:.
1913:23
1911:.
1807:79
1805:.
1782:.
1774:.
1762:.
1741:}}
1737:{{
1677:.
1666:.
1606::
1571::
1508:)
1494::
1444::
1427:)
1387:.
1308:10
1138:.
1110:.
1094:NH
1092:10
1055:.
1031:.
887:BR
802:,
798:,
794:,
790:,
786:,
782:,
778:,
774:,
770:,
766:,
762:,
758:,
754:,
750:,
746:,
742:,
738:,
734:,
730:,
726:,
722:,
718:,
714:,
710:,
706:,
702:,
698:,
680:,
676:,
672:,
617::
599:cP
571:)
564:(p
479:11
2503:.
2491::
2469:.
2464::
2439:.
2415:.
2386:.
2382::
2359:.
2355::
2349:8
2332:.
2320::
2279:.
2257::
2226:)
2222:(
2203:9
2186:.
2182::
2155:.
2151::
2128:.
2124::
2101:.
2097::
2091:9
2074:.
2060::
1990:.
1986::
1923:.
1919::
1896:.
1871:.
1850:.
1817:.
1813::
1790:.
1778::
1770::
1764:1
1747:)
1733:.
1719::
1658:-
1632:N
1486:3
1471:1
1363:N
1341:3
1330:3
1306:H
1304:5
1233:N
1128:(
1090:H
1088:5
1084:2
1080:5
1078:H
1076:5
1074:C
1007:2
992:5
990:)
988:2
951:Y
889::
853:0
846:3
839:3
569:a
566:K
482:N
476:H
473:5
470:C
370:)
366:(
132:)
Text is available under the Creative Commons Attribution-ShareAlike License. Additional terms may apply.
