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826-39-1

826-39-1 structure
826-39-1 structure
  • Name: UNII:4956DJR58O
  • Chemical Name: Mecamylamine Hydrochloride
  • CAS Number: 826-39-1
  • Molecular Formula: C11H22ClN
  • Molecular Weight: 203.752
  • Catalog: API Circulatory system medication Antihypertensive drug
  • Create Date: 2018-04-08 08:00:00
  • Modify Date: 2024-01-06 12:15:50
  • Mecamylamine hydrochloride is an orally active, nonselective, noncompetitive nAChR antagonist that can treat various neuropsychiatric disorders. Mecamylamine hydrochloride is originally used as a ganglionic blocker in treating hypertension. Mecamylamine hydrochloride can easily crosses the blood-brain barrier[1][2].
Name Mecamylamine Hydrochloride
Synonyms bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride
EINECS 212-555-8
N,2,2,3-tetramethylbicyclo[2.2.1]heptan-3-amine,hydrochloride
N,2,3,3-tétraméthylbicyclo[2.2.1]heptan-2-amine chlorhydrate
2-(Methylamino)-2,3,3-trimethylnorbornane hydrochloride
N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine hydrochloride
Norbornane, 2-(methylamino)-2,3,3-trimethyl-, hydrochloride
Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride (1:1)
N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amine hydrochloride (1:1)
N,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-aminhydrochlorid
Inversine hydrochloride
N,2,3,3-tetramethyl-2-norcamphanamine hydrochloride
UNII:4956DJR58O
MFCD00151462
Description Mecamylamine hydrochloride is an orally active, nonselective, noncompetitive nAChR antagonist that can treat various neuropsychiatric disorders. Mecamylamine hydrochloride is originally used as a ganglionic blocker in treating hypertension. Mecamylamine hydrochloride can easily crosses the blood-brain barrier[1][2].
Related Catalog
Target

nAChR[1]

In Vitro Mecamylamine blocks muscle nAChRs in a use- and voltagedependent manner. Mecamylamine blocks the nicotinic currents via trapping mechanism. The main feature of this block is the phenomenon of block relief, which might be revealed by combined action of depolarization and activation of nAChRs. The experimental study of the Mecamylamine action on muscle nAChRs revealed that: (1) Mecamylamine (1-20 μM) reduces evoked end-plate currents (EPC) amplitude with Hill’s constant equal to 1.2 and IC50 = 7.8 μM at holding potential –70 mV; (2) the calculated depth of its interaction with the muscle nAChR channel is almost half of the one of neuronal nAChRs (0.37 compare to 0.72 for neuronal nAChRs); (3) simultaneous membrane depolarization and repetitive activation of postsynaptic nAChRs by motor nerve stimulation produced rapid block relief dependent on the degree of depolarization, number of conditioning signals and Mecamylamine concentration, and only slightly depended on the rate of stimulation[2].
In Vivo Mecamylamine (0.5-1 mg/kg; Intraperitoneal injection; C57BL/6J mice) has antidepressant-like effects in both the TST and FST and these effects are dependent on bothβ2 andα7 subunits[3]. Animal Model: C57BL/6J mice (3-4 months) forced swim test (FST) and tail suspension test (TST)[3] Dosage: 0.5 mg/kg, 0.75 mg/kg, 1 mg/kg Administration: Intraperitoneal injection Result: Significantly decreased immobility time in the TST at the 1.0-mg/kg dose but did not alter baseline locomotor activity. Also significantly decreased time immobile in the FST.
References

[1]. Bacher I, et al. Mecamylamine - a nicotinic acetylcholine receptor antagonist with potential for the treatment of neuropsychiatric disorders. Expert Opin Pharmacother. 2009 Nov;10(16):2709-21.

[2]. Ostroumov K, et al. Modeling study of mecamylamine block of muscle type acetylcholine receptors. Eur Biophys J. 2008 Apr;37(4):393-402.

[3]. Rabenstein RL, et al. The nicotinic antagonist mecamylamine has antidepressant-like effects in wild-type but not beta2- or alpha7-nicotinic acetylcholine receptor subunit knockout mice. Psychopharmacology (Berl). 2006 Dec;189(3):395-401.
Boiling Point 189.3ºC at 760 mmHg
Melting Point >240ºC (dec.)
Molecular Formula C11H22ClN
Molecular Weight 203.752
Flash Point 58.1ºC
Exact Mass 203.144073
PSA 12.03000
LogP 3.61350
Storage condition Desiccate at RT
Water Solubility ethanol: 122 mg/mL

CHEMICAL IDENTIFICATION

RTECS NUMBER :
RB6900000
CHEMICAL NAME :
2-Norbornanamine, N,2,3,3-tetramethyl-, hydrochloride
CAS REGISTRY NUMBER :
826-39-1
LAST UPDATED :
199603
DATA ITEMS CITED :
12
MOLECULAR FORMULA :
C11-H21-N.Cl-H
MOLECULAR WEIGHT :
203.79
WISWESSER LINE NOTATION :
L55 ATJ CM1 C1 D1 D1 &GH

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
208 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 117,169,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
53 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,301,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
177 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 117,169,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - rat
DOSE/DURATION :
21 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,300,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
92 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
NIIRDN Drugs in Japan (Ethical Drugs). (Yakugyo Jiho Co., Ltd., Tokyo, Japan) Volume(issue)/page/year: 6,814,1982
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
17 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,300,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
81 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,300,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intravenous
SPECIES OBSERVED :
Rodent - mouse
DOSE/DURATION :
14 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
REFERENCE :
RPOBAR Research Progress in Organic-Biological and Medicinal Chemistry. (New York, NY) V.1-3, 1964-72. Discontinued. Volume(issue)/page/year: 2,300,1970
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
175 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 117,169,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Intraperitoneal
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
63 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 117,169,1956
TYPE OF TEST :
LD50 - Lethal dose, 50 percent kill
ROUTE OF EXPOSURE :
Subcutaneous
SPECIES OBSERVED :
Rodent - guinea pig
DOSE/DURATION :
155 mg/kg
TOXIC EFFECTS :
Details of toxic effects not reported other than lethal dose value
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: 117,169,1956 ** OTHER MULTIPLE DOSE TOXICITY DATA **
TYPE OF TEST :
TDLo - Lowest published toxic dose
ROUTE OF EXPOSURE :
Oral
SPECIES OBSERVED :
Mammal - dog
DOSE/DURATION :
1 gm/kg/8W-I
TOXIC EFFECTS :
Sense Organs and Special Senses (Eye) - mydriasis (pupillary dilation) Sense Organs and Special Senses (Eye) - lacrimation Nutritional and Gross Metabolic - weight loss or decreased weight gain
REFERENCE :
BJPCAL British Journal of Pharmacology and Chemotherapy. (London, UK) V.1-33, 1946-68. For publisher information, see BJPCBM. Volume(issue)/page/year: 13,501,1958
Symbol GHS06
GHS06
Signal Word Danger
Hazard Statements H301-H315-H319-H335
Precautionary Statements Missing Phrase - N15.00950417-P305 + P351 + P338
Personal Protective Equipment dust mask type N95 (US);Eyeshields;Faceshields;Gloves
Hazard Codes Xn: Harmful;
Risk Phrases R22;R36/37/38
Safety Phrases 36/37/39
RIDADR UN 2811 6
WGK Germany 3
RTECS RB6900000
Hazard Class 6.1
HS Code 2921300090
HS Code 2921300090
Summary 2921300090 other cyclanic, cyclenic or cyclotherpenic mono- or polyamines, and their derivatives; salts thereof。Supervision conditions:None。VAT:17.0%。Tax rebate rate:9.0%。MFN tariff:6.5%。General tariff:30.0%

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