Vincoline - Wikipedia · Edge Rewrite

Vincoline
Names

IUPAC name Methyl (20S)-2-hydroxy-6,7-didehydro-3α,20-epoxy-2β,5α,12β,19α-aspidospermidine-3β-carboxylate
Systematic IUPAC name Methyl (3aS,3a¹S,4S,6R,6aS,11bR)-6a-hydroxy-4-methyl-6a,7,12,13-tetrahydro-1H,3a¹H,4H,6H-3a,6-methanoindolizino[1′,8′:4,5,6]oxepino[3,4-b]indole-6-carboxylate
Identifiers
CAS Number	11034-66-5
3D model (JSmol)	Interactive image
ChemSpider	2297507
PubChem CID	3032566
UNII	QLD37A79WK^Y
CompTox Dashboard (EPA)	DTXSID60911603
InChI InChI=1S/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1 Key: YOQNZWXFGROKGY-KVKBDHCBSA-N InChI=1/C21H24N2O4/c1-13-18-8-5-10-23-11-9-19(16(18)23)14-6-3-4-7-15(14)22-21(19,25)20(12-18,27-13)17(24)26-2/h3-8,13,16,22,25H,9-12H2,1-2H3/t13-,16-,18-,19+,20-,21-/m0/s1 Key: YOQNZWXFGROKGY-KVKBDHCBBE
SMILES C[C@H]1[C@]23C[C@@](O1)([C@]4([C@@]5([C@H]2N(CC5)CC=C3)c6ccccc6N4)O)C(=O)OC
Properties
Chemical formula	C₂₁H₂₄N₂O₄
Molar mass	368.433 g·mol⁻¹
Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa). Infobox references

Vincoline is an indole alkaloid isolated from Catharanthus roseus.^[1] In a mouse model, it has been found to stimulate insulin secretion.^[2]

References

[edit]

↑ Aynilian, GH; Weiss, SG; Cordell, GA; Abraham, DJ; Crane, FA; Farnsworth, NR (1974). "Catharanthus alkaloids. XXIX. Isolation and structure elucidation of vincoline". Journal of Pharmaceutical Sciences. 63 (4): 536–8. doi:10.1002/jps.2600630409. PMID 4828700.
↑ Yao, XG; Chen, F; Li, P; Quan, L; Chen, J; Yu, L; Ding, H; Li, C; Chen, L; Gao, Z; Wan, P; Hu, L; Jiang, H; Shen, X (2013). "Natural product vindoline stimulates insulin secretion and efficiently ameliorates glucose homeostasis in diabetic murine models". Journal of Ethnopharmacology. 150 (1): 285–97. doi:10.1016/j.jep.2013.08.043. PMID 24012527.

v t e Tryptamines
Tryptamines	1-Benzoyl-DMT 1-Methyl-DMT (1,N,N-TMT, 1-TMT) 1-Methyl-T 2-HO-NMT 2-Methyl-DET 2-Methyl-DiPT 2-Methyl-iPALT (ASR-3002) 2,N,N-TMT (2-methyl-DMT) 3-IAAR 4-Bromo-DMT 4-Fluoro-DMT 4-Fluoro-T 4-MeS-DMT 4-Methyl-DMT 5-Bromo-DMT 5-Bromo-T 5-Chloro-DMT 5-Chloro-T 5-CT 5-Ethyl-DMT 5-Fluoro-DET 5-Fluoro-DMT 5-Fluoro-EPT 5-Fluoro-NiPT 5-Fluoro-T 5-Me-MiPT 5-MeS-DMT 5-Methyl-DMT 5-Methyl-T 5-Nitro-T (Nitro-I) 6-Fluoro-DET 6-Fluoro-DMT 6-Fluoro-T 6-HO-DET 6-HO-DMT 6-HO-T (6-HT) 6-MeO-DMT 6-MeO-T 6-Methyl-DMT 6-Methyl-T 6,7-DHT 7-Chloro-T 7-Fluoro-T 7-HO-DMT 7-HO-T (7-HT) 7-MeO-DMT 7-MeO-T 7-Methyl-DMT 7-Methyl-T 7-Hydroxytryptophan Acetryptine (5-AT) Almotriptan Benzotript (4-CB-Trp) BGE Bretisilocin (5-fluoro-MET; GM-2505) Convolutindole A (2,4,6-TBr,1,7-DiMeO-DMT) CPI-CG-8 DALT DAT DBT Desformylflustrabromine DET (T-9) DMT-d10 (HLP004; CYB004) DHT DiPT DMT DPT E-6801 E-6837 EB-003 EiPT EPT FGIN-127 FGIN-143 GR-46611 HBL20016 (5-MeS-6-F-DMT) HBL20017 (4-F-5-MeS-DMT) Idalopirdine iPALT (ALiPT; ASR-3003) Lespedamine (1-MeO-DMT) L-694247 MBT McPT MET MiPT MPT MsBT N-Benzyltryptamine (T-NB, NB-T, NBnT) N-(2-Cyanoethyl)tryptamine (CE-T) N-DEAOP-NET N-DEAOP-NMT N-Phosphonooxymethyl-DMT (N-POM-DMT) NAT NBoc-DMT (NB-DMT) NcPT NET/NETP NPT NHT NiPT NMT NsBT NtBT PALT (ASR-3004) PiPT Rizatriptan ST-1936 (2-Me-5-Cl-DMT) Sumatriptan T-NBOMe TCS-1205 Tryptamine (T; indolylethylamine) Tryptophan (Trp) WAY-181187 Yuremamine Z2876442907 ZCZ-011 Zolmitriptan
4-Hydroxytryptamines and esters/ethers	1-Methylpsilocin (CMY-16) 4-AcO-DALT 4-AcO-DET (ethacetin, ethylacybin) 4-AcO-DiPT (ipracetin) 4-AcO-DMT (psilacetin; O-acetylpsilocin) 4-AcO-DPT (depracetin) 4-AcO-EiPT (ethipracetin) 4-AcO-EPT 4-AcO-MALT 4-AcO-McPT 4-AcO-MET (metacetin) 4-AcO-MiPT (mipracetin) 4-AcO-MPT 4-AcO-NMT 4-AcO-TMT 4-HO-5-MeO-T 4-HO-DALT (daltocin) 4-HO-DBT 4-HO-DET (ethocin; CZ-74) 4-HO-DiBT 4-HO-DiPT (iprocin) 4-HO-DPT (deprocin) 4-HO-DsBT 4-HO-EiBT (eibucin) 4-HO-EiPT 4-HO-EPT (eprocin) 4-HO-MALT (maltocin) 4-HO-MET (metocin) 4-HO-McPT 4-HO-McPeT 4-HO-MiPT (miprocin) 4-HO-MPT (meprocin) 4-HO-MsBT 4-HO-NALT 4-HO-NBnT 4-HO-NcHT 4-HO-NET 4-HO-NiPT 4-HO-NBT (4-HO-NnBT) 4-HO-NPT 4-HO-NtBT 4-HO-PiPT (piprocin) 4-HO-TMT 4-HT (dinorpsilocin) 4-MeO-DET 4-MeO-DiPT 4-MeO-DMT 4-MeO-MiPT 4-MeO-T 4-PrO-DiPT 4-PrO-DMT 4-PrO-MET 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT Aeruginascin (4-PO-TMT) Baeocystin (4-PO-NMT) Deupsilocin (HLP003; CYB003) EB-002 (EB-373) Ethocybin (4-PO-DET; CEY-19) Luvesilocin (4-GO-DiPT; RE-104; FT-104) MSP-1014 Norbaeocystin (4-PO-T) Norpsilocin (4-HO-NMT) O-4310 (1-iPrO-6-F-psilocin) Psilocin (4-HO-DMT; CX-59) Psilocybin (4-PO-DMT; CY-39) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) RE-109 (4-GO-DMT)
5-Hydroxy- and 5-methoxytryptamines	1-Acetyl-5-MeO-DMT 2-Methyl-5-HT 2-Methyl-5-MeO-DALT 4-HO-5-MeO-T 4-F-5-MeO-DMT 4,5-DHP-DMT 4,5-DHT 4,5-MDO-DMT 4,5-MDO-DiPT 5-BT 5-Ethoxy-DMT 5-HO-DET 5-HO-DiPT 5-HO-DPT 5-HO-MET 5-HO-NiPT 5-HTP (oxitriptan) 5-MeO-2-TMT 5-MeO-34MPEMT 5-MeO-7,N,N-TMT 5-MeO-DALT 5-MeO-DBT 5-MeO-DET 5-MeO-DiPT 5-MeO-DMT (N,N,O-TMS; O-methylbufotenine) 5-MeO-DPT 5-MeO-EiPT 5-MeO-EPT 5-MeO-MALT 5-MeO-MBT 5-MeO-MET 5-MeO-MiPT 5-MeO-MsBT 5-MeO-NET 5-MeO-NiPT 5-MeO-NMT (O,N-DMS) 5-MeO-NsBT 5-MeO-PiPT 5-MeO-NBpBrT 5-MeO-T (5-MT; mexamine; O-methylserotonin) 5-MeO-T-NBOMe 5-MeO-T-NB3OMe 5-MTP (cytoguardin) 5-NOT 5-PhO-T (OVT2) 5,6-DHT 5,6-DiMeO-DiPT (5,6-MeO-DiPT) 5,6-MDO-DiPT 5,6-MDO-DMT 5,6-MDO-MiPT 5,6-MeO-MiPT 5,7-DHT Arachidonoyl serotonin ASR-3001 (5-MeO-iPALT) BAB Benanserin (BAS; SQ-4788) BGC20-761 Bufotenidine (5-HTQ; N,N,N-TMS) Bufotenin (5-HO-DMT; N,N-DMS; mappine) Bufoviridine (5-SO-DMT) CP-132,484 Cqd 280 Cqd 285 Cqdd 280 Donitriptan EMDT (2-Et-5-MeO-DMT) HIOC Indorenate (TR-3369) IS-159 Isamide (N-CA-5-MT) L-741604 MS-245 N-DEAOP-5-MeO-NET N-DEAOP-5-MeO-NMT N-Feruloylserotonin (moschamine) NB-5-MeO-DALT NB-5-MeO-DMT NB-5-MeO-MiPT Norbufotenin (5-HO-NMT; NMS) O-Acetylbufotenine (5-AcO-DMT) O-Pivalylbufotenine (5-t-BuCO-DMT) Psilomethoxin (4-HO-5-MeO-DMT) Psilomethoxybin (4-PO-5-MeO-DMT) Serotonin (5-HT)
N-Acetyltryptamines	2-Iodomelatonin 2-Phenylmelatonin 5-Methoxyluzindole 6-Chloromelatonin 6-Fluoromelatonin 6-Hydroxymelatonin 6-Methoxymelatonin 6,7-Dichloro-2-methylmelatonin α-Methylmelatonin Luzindole Melatonin (N-Ac-O-Me-serotonin; N-Ac-5-MeO-T) Normelatonin (N-acetylserotonin; NAS) N-Acetyltryptamine N-Butanoylmelatonin N-Propionylmelatonin Piromelatine TIK-301 (LY-156735)
α-Alkyltryptamines	1-Methyl-AMT 2,α-DMT (2-Me-AMT) 4-HO-αET 4-HO-αMT (MP-14) 4-Methyl-αET 4-Methyl-αMT (MP-809) 5-Chloro-αET (PAL-526) 5-Chloro-αMT (PAL-542) 5-Fluoro-αET (PAL-545) 5-Fluoro-αMT (PAL-212; PAL-544) 5-Methyl-αET 6-Fluoro-αMT 7-Chloro-αMT 7-Me-αET α-Methyltryptophan (αMTP) α,N-DMT (N-Me-αMT; SKF-7024, Ro 3-1715) α,N,N-TMT (α-Me-DMT; Alpha-N) αET (etryptamine; Monase) αMT (Indopan; IT-290; 3-API; 3-IT) IPAP (α,N-DPT) N-Hydroxy-AMT Soclenicant (BNC-210; Ile–Trp) 5-Hydroxy- and 5-alkoxy-α-alkyltryptamines: 1-Pr-5-MeO-AMT 5-Allyloxy-AMT 5-Ethoxy-αMT 5-iPrO-αMT 5-MeO-αET 5-MeO-αMT (α,O-DMS; Alpha-O) α-Methyl-5-HTP α-Methylmelatonin α-Methylserotonin (5-HO-αMT; α-Me-5-HT) α,N,O-TMS (5-MeO-α,N-DMT) α,N,N,O-TeMS (5-MeO-α,N,N-TMT) AL-37350A (4,5-DHP-αMT) BW-723C86 β-Keto-α-alkyltryptamines: BK-5Br-NM-AMT BK-5Cl-NM-AMT BK-5F-NM-AMT BK-NM-AMT
α-Ketotryptamines	AB-CHMIATA ADB-FUBIATA (ADB-FUBIACA) ADB-IACA AFUBIATA CH-FUBIATA (CH-FUBIACA) CH-HEXIATA CH-IACA CH-PIATA CH-PIATA N-(4-carboxybutyl) CH-PIATA N-(4-hydroxypentyl) CHM-FUBIATA
Cyclized tryptamines	5-MeO-IsoqT Barettin BML-190 (indomethacin morpholinylamide) Cyclic 3-OHM Ergolines and lysergamides (e.g., LSD) Harmala alkaloids and β-carbolines (e.g., 5-methoxyharmalan, norharmine 6-MeO-THH, 6-methoxyharmalan, 9-Me-BC, β-carboline (norharman), fenharmane, harmaline, harmalol, harmane, harmine, LY-266,097, pinoline, tetrahydroharmine, tryptoline) Iboga alkaloids (e.g., ibogaine, ibogamine, noribogaine, tabernanthine) Ibogalogs (e.g., catharanthalog, fluorogainalog, ibogainalog, ibogaminalog (DM-506), LS-22925, noribogainalog, noribogaminalog, PHA-57378, Pharm-136, PNU-22394, tabernanthalog) Imidazolylindoles (e.g., AGH-107, AGH-192, AH-494) Metralindole Morpholinylethylindoles (e.g., mor-T, 5-MeO-mor-T) Partial ergolines and lysergamides (e.g., NDTDI, RU-27849, RU-28251, RU-28306, FHATHBIN, LY-178210, LY-301317, Bay R 1531 (LY-197206), LY-293284, 10,11-seco-LSD, 10,11-secoergoline (α,N-Pip-T), CT-5252) Pertines (e.g., alpertine, milipertine, oxypertine, solypertine) Piperidinylethylindoles (e.g., pip-T, 5-MeO-pip-T, indoramin, indolylethylfentanyl) Pyrrolidinylethylindoles (e.g., pyr-T, 4-HO-pyr-T, 5-MeO-pyr-T, 4-F-5-MeO-pyr-T, L-760790) Pyrrolidinylmethylindoles (e.g., MPMI, 4-HO-MPMI (lucigenol), 5F-MPMI, 5-MeO-MPMI, CP-122288, CP-135807, eletriptan, MSP-2020) Tetrahydrocarbazolamines (e.g., ciclindole, flucindole, frovatriptan, LY-344864, ramatroban) Tetrahydropyridinylindoles (e.g., RS134-49, RU-28253, NEtPhOH-THPI) Tetrahydropyrroloquinolines (e.g., bufothionine, O-methylnordehydrobufotenine, dehydrobufotenine) Yohimbans (e.g., yohimbine, rauwolscine, spegatrine, corynanthine, ajmalicine, reserpine, deserpidine, rescinnamine) Z5247692566
Isotryptamines	5-MeO-isoDMT 6-MeO-isoDMT isoAMT (1-API; 1-IT; α-Me-isoT) isoDMT Isotryptamine (isoT) Ro60-0175 VER-3323 Zalsupindole (DLX-001, AAZ-A-154) Cyclized isotryptamines: DLX-0002700 JRT PNU-181731
Related compounds	1-Methylmedmain 2-Azapsilocin 2,3-Dihydro-L-tryptophan 2,3-Dihydrotryptamine 2,3-Dihydro-DMT 2,3-Dihydro-NMT 2,3-Dihydro-DET 4-Aza-5-MeO-DPT 5-Aza-4-MeO-DiPT 5-HIAA 5-HIAL 5-HITCA 5-MIAL 7-Aza-5-MeO-DiPT α-Carboline γ-Carbolines (pyridoindoles) (e.g., γ-carboline, 2MePI, 8MeO-2MePI, alosetron, gevotroline, latrepirdine, lurosetron, mebhydrolin, tiflucarbine) Amedalin Benzindopyrine Benzydamine Benzofurans (e.g., 3-APB (1-oxa-AMT), 5-MeO-DiBF (1-oxa-5-MeO-DiPT), BPAP, 3-F-BPAP, dimemebfe (5-MeO-BFE; 1-oxa-5-MeO-DMT), mebfap (5-MeO-3-APB; 1-oxa-5-MeO-AMT), MiPBF (1-oxa-MiPT), oxa-noribogaine) Benzothiophenes (e.g., S-DMT (1-thia-DMT), 3-APBT (1-thia-AMT)) BMS-505130 Carmoxirole CT-4436 Daledalin Gramine Histamine Homotryptamines (e.g., HT, DMHT) I-32 IAL Indalpine Indazolethylamines (e.g., AL-34662, AL-38022A, O-methyl-AL-34662, VU6067416, YM-348) Indenylethylamines (e.g., C-DMT (1-carba-DMT)) Indolizinylethylamines (e.g., TACT908 (2ZEDMA), 1ZP2MA, 1Z2MAP1O) Indolylaminopropanes (e.g., 1-API, 2-API, 4-API, 5-API (5-IT; PAL-571), 6-API (6-IT), 7-API) Iprindole Masupirdine Medmain Methylindolylethylpyridine (IN-399) Molindone Non-tryptamine triptans (e.g., avitriptan, LY-334370, naratriptan) Ondansetron Oxazinopyridoindoles (e.g., IHCH-8134) Phenethylamines (e.g., phenethylamine, amphetamine) Piperazinylbenzisothiazoles (e.g., lurasidone, perospirone, tiospirone, ziprasidone) Piperidinylbenzimidazolines (e.g., benperidol, timiperone) Piperidinylbenzisoxazoles (e.g., iloperidone, milsaperidone, ocaperidone, paliperidone, risperidone) Piperidinylindoles (e.g., BRL-54443, LY-334370, naratriptan, sertindole, SN-22) Pirlindole Pyridinylbenzimidazoles (e.g., droperidol) Pyridinylindoles (e.g., tepirindole) Pyridopyrroloquinoxalines (e.g., IHCH-7113, IHCH-7079, IHCH-7086, lumateperone, deulumateperone, ITI-1549) Pyrrolylethylamines (e.g., 2-pyrrolylethylamine (NEA), 3-pyrrolylethylamine (3-NEA), 3-pyrrolylpropylamine) Pyrrolopyridinylethylamines (e.g., WAY-208466) Quinolinylethylamines (e.g., mefloquine) Ro60-0213 Roxindole (EMD-49980) Selisistat Tetrahydropyridinylindoles (e.g., EMD-386088, LY-367265, RU-24,969) Tetrahydropyridinylpyrrolopyridines (e.g., (R)-69 (3IQ), (R)-70, CP-93129, CP-94253) Tetrindole Tipindole Zilpaterol (RU-42173)
See also: Phenethylamines Ergolines and lysergamides Psychedelics Simple tryptamines and common derivatives

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References