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Salsolidine hydrochloride

Names

[ CAS No. ]:
63283-42-1

[ Name ]:
Salsolidine hydrochloride

[Synonym ]:
Salsolidine hydrochloride
Prestwick_860
Isoquinoline,6,7-dimethoxy-1-methyl-1,2,3,4-tetrahydro,hydrochloride
Salsolidin*HCl

Biological Activity

[Description]:

Salsolidine hydrochloride, a tetrahydroisoquinoline alkaloid, acts as a stereoselective competitive MAO A (monoamine oxidase A) inhibitor.

[Related Catalog]:

Signaling Pathways >> Neuronal Signaling >> Monoamine Oxidase
Research Areas >> Neurological Disease

[Target]

MAO A[1]


[In Vitro]

Salsolidine hydrochloride is a tetrahydroisoquinoline alkaloid, acts as a stereoselective competitive MAO A inhibitor. The R-salsolidine is more active against MAO A than S-salsolidine (Ki=6 μM and 186 μM)[1]. Salsolidine weakly inhibits the binding of δ-receptor, with a Ki of >100 μM[2]. Salsolidine has the potential of inhibiting acetylcholinestearse and butyrylcholinesterase[3].

[References]

[1]. Bembenek ME, et al. Inhibition of monoamine oxidases A and B by simple isoquinoline alkaloids: racemic and optically active 1,2,3,4-tetrahydro-, 3,4-dihydro-, and fully aromatic isoquinolines. J Med Chem. 1990 Jan;33(1):147-52.

[2]. Airaksinen MM, et al. Binding of beta-carbolines and tetrahydroisoquinolines by opiate receptors of the delta-type. Acta Pharmacol Toxicol (Copenh). 1984 Nov;55(5):380-5.

[3]. Tundis R, et al. A potential role of alkaloid extracts from Salsola species (Chenopodiaceae) in the treatment of Alzheimer's disease. J Enzyme Inhib Med Chem. 2009 Jun;24(3):818-24.

Chemical & Physical Properties

[ Boiling Point ]:
313.4ºC at 760 mmHg

[ Melting Point ]:
189-192ºC

[ Molecular Formula ]:
C12H18ClNO2

[ Molecular Weight ]:
243.73

[ Flash Point ]:
127.1ºC

[ Exact Mass ]:
243.10300

[ PSA ]:
30.49000

[ LogP ]:
3.04130

Toxicological Information

CHEMICAL IDENTIFICATION

RTECS NUMBER :
NX5018600
CHEMICAL NAME :
Isoquinoline, 1,2,3,4-tetrahydro-6,7-dimethoxy-1-methyl-, hydrochloride
CAS REGISTRY NUMBER :
63283-42-1
LAST UPDATED :
198806
DATA ITEMS CITED :
1
MOLECULAR FORMULA :
C12-H17-N-O2.Cl-H
MOLECULAR WEIGHT :
243.76

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
189 mg/kg
TOXIC EFFECTS :
Behavioral - convulsions or effect on seizure threshold Lungs, Thorax, or Respiration - dyspnea
REFERENCE :
JPETAB Journal of Pharmacology and Experimental Therapeutics. (Williams & Wilkins Co., 428 E. Preston St., Baltimore, MD 21202) V.1- 1909/10- Volume(issue)/page/year: 76,263,1942

Synthetic Route

Click to get detail synthetic route

Precursor & DownStream

Precursor

DownStream

Related Compounds

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