Home > Name List By m > methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20, 21-dodecahydroyohimban-19-carboxylate

CAS No 146-48-5 , methyl
(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,
21-dodecahydroyohimban-19-carboxylate

  • Name: methyl
    (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,
    21-dodecahydroyohimban-19-carboxylate
  • Synonyms: Aphrodyne; Yocon; Corynine;methyl
    (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,
    21-dodecahydroyohimban-19-carboxylate; APHRODINE; Yohimex; Quebrachine; Aphrosol; Quebrachin;Yohimbin;
  • CAS Registry Number:
  • Transport: 1544
  • Melting Point: 231-233 °C(lit.)
  • Density: 1.31 g/cm3
  • Refractive index: 1.66
  • Safety Statements: Poison by ingestion, subcutaneous, intravenous, and intraperitoneal routes. Experimental reproductive effects. Human systemic effects: ataxia, heart rate changes, paresthesia.Cases of poisoning have occurred from its use as an aphrodisiac. Upon local application it produces anesthesia. However, absorption of it can give rise to toxic symptoms, such as salivation, increased respiration, and diarrhea. With reference to the circulatory system, there may be a fall in blood pressure and sometimes myocardial damage, involving particularly the conduction system of the heart, with a resultant decrease in the efficiency of the heart. An adrenergic blocker used to treat arteriosclerosis and angina pectoris. Formerly used as a local anesthetic and mydriatic (pupillary dilator). When heated to decomposition it emits toxic fumes of NOx.
  • Hazard Symbols: Said to be an aphrodisiac. Toxic by ingestion.
  • EINECS: 205-672-0
  • Molecular Weight: 354.44274
  • InchiKey: BLGXFZZNTVWLAY-SCYLSFHTSA-N
  • InChI: InChI=1S/C21H26N2O3/c1-26-21(25)19-15-10-17-20-14(13-4-2-3-5-16(13)22-
    20)8-9-23(17)11-12(15)6-7-18(19)24/h2-5,12,15,17-19,22,24H,6-11H2,
    1H3/t12-,15-,17-,18-,19+/m0/s1
  • Risk Statements: 23/24/25-39
  • Molecular Formula: C21H26N2O3
  • Molecular Structure:CAS No:146-48-5 methyl<br />(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,<br />21-dodecahydroyohimban-19-carboxylate

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  • China Xi'an HaoTian Bio-engineering Co., Ltd [Manufacturers]
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References of methyl
(1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,
21-dodecahydroyohimban-19-carboxylate
Title: Yohimbine
CAS Registry Number: 146-48-5
CAS Name: (16a,17a)-17-Hydroxyyohimban-16-carboxylic acid methyl ester
Synonyms: quebrachine; corynine; aphrodine
Molecular Formula: C21H26N2O3
Molecular Weight: 354.44
Percent Composition: C 71.16%, H 7.39%, N 7.90%, O 13.54%
Literature References: Indole alkaloid with a2-adrenergic blocking activity. Found in Corynanthe johimbe K. Schum., Rubiaceae and related trees, also in Rauwolfia serpentina (L.) Benth., Apocynaceae: Raymond-Hamet, J. Pharm. Chim. 19, 209 (1934); Hofmann, Helv. Chim. Acta 37, 849 (1954); Stoll, Jucker, Ullmanns Encyklop?die der technischen Chemie vol. 3 (Munich, 3rd ed., 1953) p 266; Bader et al., J. Am. Chem. Soc. 76, 1695 (1954). Structure: Witkop, Ann. 554, 83 (1943); Clemo, Swan, J. Chem. Soc. 1946, 617. Stereochemistry: Janot et al., Bull. Soc. Chim. Fr. 1952, 1085; Godfredsen, Vandegal, Acta Chem. Scand. 10, 1414 (1956); Van Tamelen et al., J. Am. Chem. Soc. 78, 4628 (1956); Ban, Yonemitsu, Tetrahedron 20, 2877 (1964). Synthesis: Van Tamelen et al., J. Am. Chem. Soc. 80, 5006 (1958); Liljegren, Potts, J. Org. Chem. 27, 377 (1962). Total synthesis: Van Tamelen et al., J. Am. Chem. Soc. 91, 7315 (1969); Stork, Guthikonda, ibid. 94, 5109 (1972); T. Kametani et al., Chem. Pharm. Bull. 24, 2500 (1976); E. Wenkert et al., J. Am. Chem. Soc. 100, 4894 (1978); 101, 5370 (1979); 104, 2244 (1982); I. Ninomiya et al., Heterocycles 14, 631 (1980). Pharmacokinetics in humans: J. A. Owen et al., Eur. J. Clin. Pharmacol. 32, 577 (1987). Clinical studies in impotence: K. Reid et al., Lancet 2, 421 (1987); A. Morales et al., J. Urol. 137, 1168 (1987). Review of pharmacology and use in molecular studies of a2-adrenoreceptor: M. R. Goldberg, D. Robertson, Pharmacol. Rev. 35, 143-180 (1987). Comprehensive description: A. G. Mekkawi, A. A. Al-Badr, Anal. Profiles Drug Subs. 16, 731-768 (1986).
Properties: Orthorhombic needles from dil alc, mp 234°. Also mp 235-237°. [a]D20 +50.9 to +62.2° (ethanol); [a]D20 +108° (pyridine); [a]20546 +129° (c = 0.5 in pyridine). uv max (methanol): 226, 280, 291 nm (log e 4.56, 3.88, 3.80). Sparingly sol in water. Sol in alcohol, chloroform, hot benzene; moderately sol in ether.
Melting point: mp 234°; mp 235-237°
Optical Rotation: [a]D20 +50.9 to +62.2° (ethanol); [a]D20 +108° (pyridine); [a]20546 +129° (c = 0.5 in pyridine)
Absorption maximum: uv max (methanol): 226, 280, 291 nm (log e 4.56, 3.88, 3.80)
 
Derivative Type: Hydrochloride
CAS Registry Number: 65-19-0
Trademarks: Antagonil (Wildlife Pharm.); Aphrodyne (Star); Erex (Ion); Yobine (Lloyd); Yocon (Palisades); Yohimex (Kramer); Yohydrol (Riedel-Zabinka); Yovital (Kenwood)
Molecular Formula: C21H26N2O3.HCl
Molecular Weight: 390.90
Percent Composition: C 64.52%, H 6.96%, N 7.17%, O 12.28%, Cl 9.07%
Properties: Orthorhombic plates, prisms from alc; dec 302°. [a]D22 +105° (H2O). Sol in ~120 ml water, 400 ml alc. The aq soln is about neutral.
Optical Rotation: [a]D22 +105° (H2O)
 
Use: Pharmacological probe for the study of a2-adrenoceptor.
Therap-Cat: Mydriatic. In treatment of impotence.
Therap-Cat-Vet: Xylazine reversing agent.
Keywords: a-Adrenergic Blocker; Mydriatic.