Yohimbine

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Names

[ CAS No. ]:
146-48-5

[ Name ]:
Yohimbine

[Synonym ]:
[3H]-Yohimbine
Aphrosol
Methyl (16α,17α)-17-hydroxyyohimban-16-carboxylate
Yohimban-16α-carboxylic acid, 17α-hydroxy-, methyl ester (8CI)
corynine
yohimbine
(16α,17α)-17-Hydroxy-yohimban-16-carboxylic acid methyl ester
quebrachine
Yohimban-16-carboxylic acid, 17-hydroxy-, methyl ester, (16α,17α)-
Quebrachin
Yohimbine HCl
(16a,17a)-17-Hydroxyyohimban-16-carboxylic Acid Methyl Ester
Yohimex
Yocon
APHRODINE
methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate
MFCD00042748
Yohimban-16-α-carboxylic acid, 17-α-hydroxy-, methyl ester
EINECS 205-672-0
(+)-Yohimbin
Aphrodyne
Yohimbin

Chemical & Physical Properties

[ Density]:
1.3±0.1 g/cm3

[ Boiling Point ]:
543.0±50.0 °C at 760 mmHg

[ Melting Point ]:
231-233 °C(lit.)

[ Molecular Formula ]:
C21H26N2O3

[ Molecular Weight ]:
354.443

[ Flash Point ]:
282.2±30.1 °C

[ Exact Mass ]:
354.194336

[ PSA ]:
65.56000

[ LogP ]:
2.20

[ Vapour Pressure ]:
0.0±1.5 mmHg at 25°C

[ Index of Refraction ]:
1.661

[ Storage condition ]:
Store at RT

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
ZG1000000
CHEMICAL NAME :
Yohimban-16-alpha-carboxylic acid, 17-alpha-hydroxy-, methyl ester
CAS REGISTRY NUMBER :
146-48-5
BEILSTEIN REFERENCE NO. :
0097276
LAST UPDATED :
199612
DATA ITEMS CITED :
8
MOLECULAR FORMULA :
C21-H26-N2-O3
MOLECULAR WEIGHT :
354.49
WISWESSER LINE NOTATION :
T F6 D5 C666 EM ON&&TTTJ TQ UVO1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Human - woman
DOSE/DURATION :
5 gm/kg
TOXIC EFFECTS :
Peripheral Nerve and Sensation - paresthesis Behavioral - ataxia Cardiac - change in rate
REFERENCE :
AEMED3 Annals of Emergency Medicine. (American College of Emergency Physicians, 1125 Executive Circle, Irving, TX 75038) Volume(issue)/page/year: 14,1002,1985
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
43 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 5,432,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
16 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 5,432,1955
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
37 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
ARZNAD Arzneimittel-Forschung. Drug Research. (Editio Cantor Verlag, Postfach 1255, W-7960 Aulendorf, Fed. Rep. Ger.) V.1- 1951- Volume(issue)/page/year: 5,432,1955
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
50 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1418,1935
TYPE OF TEST :
LDLo - Lowest published lethal dose
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rabbit
DOSE/DURATION :
11 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
HBAMAK "Abdernalden's Handbuch der Biologischen Arbeitsmethoden." (Leipzig, Ger. Dem. Rep.) Volume(issue)/page/year: 4,1418,1935 ** REPRODUCTIVE DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Intraperitoneal
DOSE :
1 mg/kg
SEX/DURATION :
male 1 day(s) pre-mating
TOXIC EFFECTS :
Reproductive - Paternal Effects - other effects on male
REFERENCE :
NLETDU Neuroendocrinology Letters. (Brain Research Promotion, D-7400, Tubingen, Germany) V.1- 1979- Volume(issue)/page/year: 12,69,1990 *** NIOSH STANDARDS DEVELOPMENT AND SURVEILLANCE DATA *** NIOSH OCCUPATIONAL EXPOSURE SURVEY DATA : NOHS - National Occupational Hazard Survey (1974) NOHS Hazard Code - 84715 No. of Facilities: 68 (estimated) No. of Industries: 1 No. of Occupations: 6 No. of Employees: 2770 (estimated)

Safety Information

[ Hazard Codes ]:
T

[ Risk Phrases ]:
R23/24/25

[ Safety Phrases ]:
S27-S36/37/39-S45

[ RIDADR ]:
1544

[ RTECS ]:
ZG1000000

[ Packaging Group ]:
II

[ Hazard Class ]:
6.1(a)

Synthetic Route

Precursor & DownStream

Precursor

  • 17-Oxoyohimban-16α-carboxylic acid methyl ester
  • 18,19-Didehydroyohimban-17-one
  • (4aS,6S,7R,8aR)-2-(2-(1H-indol-3-yl)ethyl)-7-hydroxy-3-oxodecahydroisoquinolin-6-yl pivalate
  • dimethyl (16α)-18,19-didehydro-17-oxoyohimban-1,16-dicarboxylate
  • Secologanin
  • O',O',O',O'-tetraacetylsecologanin

DownStream

  • Propanoic acid,2-(2,4,5-trichlorophenoxy)-, (2R)-
  • Isoquinoline
  • Harmane
  • 3-ethylindole
  • Indole-2-carboxylic acid
  • Ketoyobirine
  • Yobirine

Related Compounds

  • yohimbine
  • b-Yohimbine
  • a-Yohimbine
  • d-Yohimbine
  • d-Yohimbine
  • Yohimbine-d3
  • (R)-Tetrahydro-2'H-spiro[cyclopropane-1,6'-pyrrolo[1,2-a]pyrazin]-3'(4'H)-one
  • 3-((3-Methoxypropyl)amino)thietane1,1-dioxide
  • N-(4-(Methylthio)butyl)thietan-3-amine
  • N-(2-(1,1-Dioxidothietan-3-yl)ethyl)propionamide
  • 3-((4-Methylpentyl)amino)thietane1,1-dioxide
  • (6S)-1-Methyl-3-tosyl-3-azabicyclo[4.1.0]heptane-6-carbaldehyde
  • (S)-8A-methylhexahydropyrrolo[1,2-a]pyrazin-3(4H)-one
  • Imino(methyl)(pyrrolidin-3-YL)-L6-sulfanone
  • 4-(Methylthio)-2-(thietan-3-ylamino)butan-1-ol
  • 2-(3,5-Dimethylcyclohexyl)-2-methylpropanal
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