methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate hydrochloride

• ChemBase ID: 72997
• Molecular Formular: C21H27ClN2O3
• Molecular Mass: 390.90368
• Monoisotopic Mass: 390.17102041
• SMILES: [nH]1c2c(c3c1cccc3)CCN1[C@H]2C[C@H]2[C@H](C1)CC[C@@H]([C@@H]2C(=O)OC)O.Cl
• Canonical SMILES: COC(=O)[C@H]1[C@@H](O)CC[C@@H]2[C@@H]1C[C@@H]1N(C2)CCc2c1[nH]c1c2cccc1.Cl
• InChI: InChI=1S/C21H26N2O3.ClH/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;1H/t12-,15-,17-,18-,19+;/m0./s1
• InChIKey: PIPZGJSEDRMUAW-VJDCAHTMSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^{2,10}.0^{4,9}.0^{15,20}]henicosa-2(10),4,6,8-tetraene-19-carboxylate hydrochloride; methyl (1S,15R,18S,19R,20S)-18-hydroxy-3,13-diazapentacyclo[11.8.0.0^2,^1^0.0^4,^9.0^1^5,^2^0]henicosa-2(10),4,6,8-tetraene-19-carboxylate hydrochloride
• IUPAC Traditional name: yohimbine hydrochloride
• Synonyms: Antagonil; Yohimbe; Aphrodine hydrochloride; Yohimbine monohydrochloride; Yohimbine hydrochloride; Giemsa Stain; (16α,17α)-17-Hydroxy-yohimban-16-carboxylic Acid Methyl Ester Hydrochloride; Actibine; Aphrodyne; Dayto-Himbin; Erex; NIH 9689; NSC 19509; Thybine; Yocon; Yohimbine Chloride; Yohimex; Yomax; 17-Hydroxyyohimban-16-carboxylic acid methyl ester hydrochloride; Yohimbine hydrochloride; (1R,2S,4aR,13bS,14aS)-methyl 2-hydroxy-1,2,3,4,4a,5,7,8,13,13b,14,14a-dodecahydroindolo[2',3':3,4]pyrido[1,2-b]isoquinoline-1-carboxylate hydrochloride; 姬姆氏色素

Database IDs

• CAS Number: 65-19-0; 51811-82-6
• EC Number: 257-438-2; 200-600-4
• MDL Number: MFCD00081642; MFCD00012674
• PubChem SID: 24277814; 162037917
• PubChem CID: 6169

CALCULATED PROPERTIES

• Acid pKa: 14.676982
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -0.037232514
• LogD (pH = 7.4): 1.6539497
• Log P: 2.0986583
• Molar Refractivity: 99.631 cm^3
• Polarizability: 40.114906 Å^3
• Polar Surface Area: 65.56 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; H2O: soluble10 mg/mL; Methanol
• Apperance: Pale Beige Solid; white to off-white powder
• Melting Point: 266-269°C; 288-290 °C (dec.)(lit.); ca 300°C

Safety Information

• Storage Condition: -20°C; Refrigerator
• RTECS: ZG1015000
• European Hazard Symbols: Toxic (T)
• UN Number: 1544
• German water hazard class: 3
• Hazard Class: 6.1
• Packing Group: 2
• Risk Statements: 23/24/25
• Safety Statements: 22-36/37/39-45
• TSCA Listed: 是
• GHS Pictograms: GHS06
• GHS Signal Word: Danger
• GHS Hazard statements: H300-H311-H331
• GHS Precautionary statements: P261-P264-P280-P301 + P310-P311
• Personal Protective Equipment: Eyeshields, Faceshields, Gloves, type P2 (EN 143) respirator cartridges
• RID/ADR: UN 1544 6.1/PG 2

Pharmacology Properties

• Gene Information: human ... ADRA2A(150), ADRA2B(151), ADRA2C(152)

Product Information

• Purity: ≥98% (TLC)
• Salt Data: HCl; ydrochloride
• Classification: Genuine Natural Compounds

DETAILS

Selleck Chemicals - S2373

Research Area: Endocrinology
Biological Activity:
Yohimbine(Antagonil) has been used as a mydriatic and in the treatment of impotence. It is also alleged to be an aphrodisiac. Yohimbine is a pre-synaptic alpha 2-adrenergic blocking agent. Yohimbine may exert its beneficial effect on erectile ability through blockade of central alpha 2-adrenergic receptors producing an increase in sympathetic drive secondary to an increase in norepinephrine release and in firing rate of cells in the brain noradrenergic nuclei. [1]

Sigma Aldrich - Y3125

Biochem/physiol Actions
α2-adrenoceptor antagonist.

Toronto Research Chemicals - Y100800

Indole alkaloid with α2-adrenergic blocking activity. Mydriatic. Used in the treatment of neurological disorders.

REFERENCES

• http://www.drugbank.ca/drugs/DB01392
• Mekkawi, A.G., Anal. Profile Drug Subs., 16, 731 (1986)
• Goldberg, M.R., et al.: Pharmacol. Rev., 35, 143 (1986)
• Morales, A., et al.: J. Urol., 137, 1168 (1986)