(-)-Mecamylamine Hydrochloride

Base Information

• Chemical Name: (-)-Mecamylamine Hydrochloride
• CAS No.: 107596-31-6
• Molecular Formula: C₁₁H₂₁N*ClH
• Molecular Weight: 203.755
• European Community (EC) Number: 687-704-7
• UNII: 8Y5C5OWB4R
• DSSTox Substance ID: DTXSID60493914
• Wikidata: Q27271191
• Mol file: 107596-31-6.mol

Synonyms:107596-31-6;(-)-Mecamylamine Hydrochloride;R-(-)-Mecamylamine Hydrochloride;Mecamylamine hydrochloride, (-)-;NIH-11009;TC-5213;8Y5C5OWB4R;(1S,2R,4R)-N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine Hydrochloride;Mecamylamine R-(-)-form hydrochloride [MI];(1S,2R,4R)-N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine;hydrochloride;Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride, (1S-exo)-;UNII-8Y5C5OWB4R;Mecamylamine hydrochloride, (R)-;Mecamylamine hydrochloride, R-(-)-;starbld0000190;(R)-mecamylamine hydrochloride;DTXSID60493914;Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride,;EN300-20098150;Q27271191;(1S,2R,4R)-N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine--hydrogen chloride (1/1)

Chemical Property of (-)-Mecamylamine Hydrochloride

Chemical Property:

• PSA: 12.03000
• LogP: 3.61350
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 1
• Rotatable Bond Count: 1
• Exact Mass: 203.1440774
• Heavy Atom Count: 13
• Complexity: 197

Purity/Quality:

97% ^*data from raw suppliers

R-(-)-MecamylamineHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC1(C2CCC(C2)C1(C)NC)C.Cl
• Isomeric SMILES: C[C@]1([C@H]2CC[C@H](C2)C1(C)C)NC.Cl
• Uses: The R-(+) enantiomer of Mecamylamine (M202600), a noncompetitive neuronal nicotinic receptor modulator

Technology Process of (-)-Mecamylamine Hydrochloride

There total 19 articles about (-)-Mecamylamine 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: 100.0%

N,2-endo,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine → N,2-endo,3,3-tetramethylbicyclo[2.2.1]heptan-2-aminium chloride (107596-31-6)

Guidance literature:

With hydrogenchloride; In diethyl ether;

DOI:10.1039/C6OB01974A

Reference yield: 64.0%

sodium ethanolate (141-52-6) + (1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine (107485-87-0) → (1S)-N-1-Phenethyl-3-hydroxy-2,2-dimethylpropanamide (33290-12-9) + S-(+)-mecamylamine hydrochloride (107596-31-6)

Guidance literature:

In ethanol; for 0.75h; Heating;

DOI:10.1002/hlca.19860690620

Reference yield: 56.0%

N-(3,3-dimethylbicyclo[2.2.1]heptan-2-ylidene)methanamine + methyllithium (917-54-4) → N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-aminium chloride (107596-31-6)

Guidance literature:

N-(3,3-dimethylbicyclo[2.2.1]heptan-2-ylidene)methanamine; With boron trifluoride diethyl etherate; Inert atmosphere;

methyllithium; In diethyl ether; at 0 - 20 ℃; for 1h; Inert atmosphere;

With hydrogenchloride; In diethyl ether;

DOI:10.1039/C6OB01974A

upstream raw materials:

(+/-)-mecamylamine

sodium ethanolate

(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine

(+/-)-exo-mecamylamine hydrochloride

Downstream raw materials:

(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine