methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

Base Information

• Chemical Name: methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride
• CAS No.: 65-19-0
• Molecular Formula: C21H26N2O3.ClH
• Molecular Weight: 390.91
• Hs Code.: 29339900
• NSC Number: 757411
• Mol file: 65-19-0.mol

Synonyms:methyl (1S,15R,18S,19R,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-3-ium-19-carboxylate;chloride;methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride;SR-05000001746;SPECTRUM1500663;SCHEMBL6515647;HMS1921A04;Pharmakon1600-01500663;CCG-40055;NSC757411;NSC-757411;SR-05000001746-2

Chemical Property of methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

Chemical Property:

• Appearance/Colour: Very slightly yellow needles.
• Vapor Pressure: 0mmHg at 25°C
• Melting Point: 288-290 °C (dec.)(lit.)
• Refractive Index: 103 ° (C=1, H2O)
• Boiling Point: 543 °C at 760 mmHg
• Flash Point: 282.2 °C
• PSA: 65.56000
• LogP: 3.38700
• Storage Temp.: Refrigerator
• Sensitive.: Light Sensitive
• Solubility.: H2O: 10 mg/mL
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 2
• Exact Mass: 390.1710204
• Heavy Atom Count: 27
• Complexity: 555

Purity/Quality:

98% ^*data from raw suppliers

Yohimbine hydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s): T
• Hazard Codes: T
• Statements: 23/24/25-33-23/24
• Safety Statements: 22-36/37/39-45-24/25

MSDS Files:

SDS file from LookChem

Total 1 MSDS from other Authors

Useful:

• Canonical SMILES: COC(=O)C1C(CCC2C1CC3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• Isomeric SMILES: COC(=O)C1[C@H](CC[C@@H]2[C@@H]1C[C@H]3C4=C(CCN3C2)C5=CC=CC=C5N4)O.Cl
• Uses: Yohimbine hydrochloride is an Indole alkaloid with α2-adrenergic blocking activity. It is an alpha adrenergic blocker, mydriatic, antidepressant that used in the treatment of neurological disorders and erectile dysfunction. Yohimbine hydrochloride is an α2-adrenergic receptor antagonist. It blocks the central α2-adrenegic receptors in the brain, thus preventing and reducing the effects of xylazine, an α2-adrenergic agonist. The sedative effects and respiratory depression that accompany xylazine administration are both antagonized and reversed by yohimbine. Yohimbine hydrochloride also produces an antidiuretic effect, and increases heart rate and blood pressure.

Technology Process of methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride

There total 1 articles about methyl (1S,15R,18S,20S)-18-hydroxy-1,3,11,12,14,15,16,17,18,19,20,21-dodecahydroyohimban-19-carboxylate;hydrochloride which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield:

rauwolscine (131-03-3) → rauwolscine hydrochloride (65-19-0)

Guidance literature:

With hydrogenchloride; In water; pH=2 - 2.5;

Reference yield:

yohimbine (65-19-0) → yohimbinic acid (522-87-2)

Guidance literature:

With sodium hydroxide; In methanol; water;

Reference yield:

yohimbine (65-19-0) → 1-(p-nitrobenzyloxy)yohimbine

Guidance literature:

Multi-step reaction with 2 steps

1.1: NaBH₃CN / trifluoroacetic acid / 3 h / 20 °C

1.2: 86 percent / Na₂WO₄*2H₂O; H₂O₂ / H₂O; methanol / 1 h / 0 °C

2.1: 90 percent / K₂CO₃ / dimethylformamide / 0.5 h / 20 °C

With sodium cyanoborohydride; potassium carbonate; In N,N-dimethyl-formamide; trifluoroacetic acid;

DOI:10.3987/COM-06-S(O)26

upstream raw materials:

rauwolscine

Downstream raw materials:

10-Hydroxyyohimbine

11-hydroxy-yohimbine

yohimbinic acid

Refernces