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Substance Name: Rescinnamine [INN:BAN:JAN:NF]
RN: 24815-24-5
UNII: Q6W1F7DJ2D
InChIKey: SZLZWPPUNLXJEA-QEGASFHISA-N

Classification Codes

  • Antihypertonic
  • Drug / Therapeutic Agent
  • Human Data
  • Reproductive Effect
  • Sedative

Molecular Formula

  • C35-H42-N2-O9

Molecular Weight

  • 634.7218
 
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Names and Synonyms

Name of Substance

  • Rescinnamine
  • Rescinnamine [INN:BAN:JAN:NF]

Synonyms

  • 11,17alpha-Dimethoxy-18beta-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-3beta,20alpha-yohimban-16beta-carboxylic acid methyl ester
  • 3,4,5-Trimethoxycinnamic acid, methyl reserpate
  • 3,4,5-Trimethoxycinnamoyl methyl reserpate
  • 3,4,5-Trimethylcinnamic acid, ester with methyl reserpate
  • 3,4,5-Trimethylcinnamoyl methyl reserpate
  • 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester), (E)-
  • 4-25-00-01323 (Beilstein Handbook Reference)
  • AI3-52763
  • Anaprel
  • Apolon
  • Apoterin
  • BRN 0075328
  • Cartric
  • CCRIS 4711
  • Cinamine
  • Cinatabs
  • Cinnaloid
  • Cinnasil
  • EINECS 246-471-8
  • HSDB 2176
  • Methyl 18-O-(3,4,5-trimethoxycinnamoyl)reserpate
  • Methyl 1alpha,2beta,3alpha,4,4aalpha,5,7,8,13,13bbeta,14,14aalpha-dodecahydro-2alpha,11-dimethoxy-3beta-(3,4,5-trimethoxycinnamoyloxy)benz(g)indolo(2,3-a)quinolizine-1beta-carboxylate
  • Methyl reserpate 3,4,5-trimethoxycinnamic acid ester
  • Methyl trimethoxycinnamoylreserpate
  • Moderil
  • Normorescina
  • NSC 15628
  • Paresinan
  • Raupyrol
  • Raurescin
  • Raurescine
  • Recinnamine
  • Recitensina
  • Rescaloid
  • Rescamin
  • Rescidan
  • Rescin
  • Rescinamina
  • Rescinamina [INN-Spanish]
  • Rescinnamin
  • Rescinnamina
  • Rescinnamina [DCIT]
  • Rescinnamine
  • Rescinnamine (VAN)
  • Rescinnaminum
  • Rescinnaminum [INN-Latin]
  • Rescinpal
  • Rescisan
  • Rescitens
  • Resealoid
  • Resepinine (C35 alkaloid)
  • Reserpinene
  • Reserpinin
  • Reserpinine
  • Reserpinine (C35 alkaloid)
  • Reserpinine (VAN)
  • Resipal
  • Reskinnamin
  • Rozex
  • Scinnamina
  • Tenamine
  • Trimethoxy cinnamoyl reserpate de methyl
  • Trimethoxy cinnamoyl reserpate de methyl [French]
  • Trimethoxycinnamoyl methyl reserpate
  • Tuareg
  • UNII-Q6W1F7DJ2D
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)-oxy)-, methyl ester, (3beta,16beta,17alpha,18beta(E),20alpha)-

Systematic Names

  • 3-beta,20-alpha-Yohimban-16-beta-carboxylic acid, 18-beta-hydroxy-11,17-alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
  • 3beta,20alpha-Yohimban-16beta-carboxylic acid, 18beta-hydroxy-11,17alpha-dimethoxy-, methyl ester, 3,4,5-trimethoxycinnamate (ester)
  • Methyl 18beta-hydroxy-11,17alpha-dimethoxy-3beta,20alpha-yohimban-16beta-carboxylate
  • Rescinnamine
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-(((2E)-1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-
  • Yohimban-16-carboxylic acid, 11,17-dimethoxy-18-((1-oxo-3-(3,4,5-trimethoxyphenyl)-2-propenyl)oxy)-, methyl ester, (3beta,16beta,17alpha,18beta,20alpha)-

Registry Numbers

CAS Registry Number

  • 24815-24-5

FDA UNII

  • Q6W1F7DJ2D

Other Registry Numbers

  • 15676-43-4
  • 15676-44-5
  • 25460-29-1
  • 28821-79-6
  • 412909-15-0
  • 522-78-1
  • 84-34-4

System Generated Number

  • 0024815245

Structure Descriptors

InChI

1S/C35H42N2O9/c1-40-21-8-9-22-23-11-12-37-18-20-15-29(46-30(38)10-7-19-13-27(41-2)33(43-4)28(14-19)42-3)34(44-5)31(35(39)45-6)24(20)17-26(37)32(23)36-25(22)16-21/h7-10,13-14,16,20,24,26,29,31,34,36H,11-12,15,17-18H2,1-6H3/b10-7+/t20-,24+,26-,29-,31+,34+/m1/s1

InChIKey

SZLZWPPUNLXJEA-QEGASFHISA-N

Smiles

c12[C@@H]3[N@@](C[C@@H]4[C@H](C3)[C@@H]([C@H]([C@@H](C4)OC(=O)\C=C\c3cc(c(OC)c(c3)OC)OC)OC)C(OC)=O)CCc1c1c([nH]2)cc(cc1)OC

Toxicity

Organism Test Type Route Reported Dose (Normalized Dose) Effect Source
guinea pig LDLo intravenous 35mg/kg (35mg/kg)   Arzneimittel-Forschung. Drug Research. Vol. 23, Pg. 600, 1973.
human TDLo oral 4ug/kg/D (0.004mg/kg) SENSE ORGANS AND SPECIAL SENSES: OTHER CHANGES: OLFACTION

BEHAVIORAL: SOMNOLENCE (GENERAL DEPRESSED ACTIVITY)

BEHAVIORAL: ANTIPSYCHOTIC
"Toxicology of Drugs and Chemicals," Deichmann, W.B., New York, Academic Press, Inc., 1969Vol. -, Pg. 517, 1969.
mouse LD50 intraperitoneal 65mg/kg (65mg/kg)   French Medicament Patent Document. Vol. #5226M,
mouse LD50 intravenous 56mg/kg (56mg/kg)   U.S. Army Armament Research & Development Command, Chemical Systems Laboratory, NIOSH Exchange Chemicals. Vol. NX#00965,
mouse LD50 oral 1420mg/kg (1420mg/kg)   "Psychotropic Drugs and Related Compounds," 2nd ed., Usdin, E., and D.H. Efron, Washington, DC, 1972Vol. -, Pg. 109, 1972.
mouse LD50 subcutaneous 263mg/kg (263mg/kg)   French Medicament Patent Document. Vol. #5226M,
rat LD50 intraperitoneal 250mg/kg (250mg/kg)   Drugs in Japan Vol. 6, Pg. 898, 1982.
rat LD50 oral 1gm/kg (1000mg/kg)   Drugs in Japan Vol. 6, Pg. 898, 1982.
rat LD50 subcutaneous 540mg/kg (540mg/kg)   Drugs in Japan Vol. 6, Pg. 898, 1982.

Physical Properties

Physical Property Value Units Temp (deg C) Source
Melting Point 238.5 deg C   EXP
log P (octanol-water) 3.850 (none)   EST
Atmospheric OH Rate Constant 5.05E-10 cm3/molecule-sec 25 EST

Physical property data is provided to ChemIDplus by SRC, Inc.