- Mecamylamine
- Mecamylamine hydrochloride
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| Name |
Mecamylamine hydrochloride |
EINECS | 212-555-8 |
| CAS No. | 826-39-1 | Density | N/A |
| PSA | 12.03000 | LogP | 3.61350 |
| Solubility | ethanol: 122 mg/mL | Melting Point |
>240 °C (dec.) |
| Formula | C11H21N.HCl | Boiling Point | 189.3 °C at 760 mmHg |
| Molecular Weight | 203.79 | Flash Point | 58.1 °C |
| Transport Information | UN 2811 6.1/PG 3 | Appearance | white solid |
| Safety | 36/37/39 | Risk Codes | 22-36/37/38 |
| Molecular Structure |
|
Hazard Symbols |
 Xn
|
| Synonyms |
2-Norbornanamine,N,2,3,3-tetramethyl-, hydrochloride (8CI);Bicyclo[2.2.1]heptan-2-amine,N,2,3,3-tetramethyl-, hydrochloride (9CI);CPDD 0059;Inversine;Mecamylaminechloride;Mevasin;Mevasine;N,2,3,3-Tetramethyl-2-norbornanamine hydrochloride; |
Mecamylamine hydrochloride Synthetic route
- 826-39-1
(+/-)-exo-mecamylamine hydrochloride
- 14649-03-7
(S)-phenylethyl isocyanate
B
- 107485-87-0
(1R,2R,4S)-N-<((S)-1-phenylethyl)carbamoyl>mecamylamine
| Conditions | Yield |
|---|---|
| With sodium carbonate 2.) CHCl3, 1 h, room t.; Yield given. Multistep reaction. Yields of byproduct given; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
| Conditions | Yield |
|---|---|
| With potassium hydrogencarbonate In tetrahydrofuran; N,N-dimethyl-formamide Alkylation; Heating; |
- 826-39-1
(+/-)-exo-mecamylamine hydrochloride
| Conditions | Yield |
|---|---|
| Multi-step reaction with 2 steps 1: 1.) aq. Na2CO3 / 2.) CHCl3, 1 h, room t. 2: 64 percent / ethanol / 0.75 h / Heating View Scheme |
Mecamylamine hydrochloride Chemical Properties
Chemistry informtion about Mevasin Hydrochloride (CAS NO.826-39-1) is:
IUPAC Name: N,5,6,6-Tetramethylbicyclo[2.2.1]Heptan-5-Amine Hydrochloride
Synonyms: N,2,3,3-Tetramethylbicyclo[2.2.1]Heptan-2-Amine Hydrochloride ; Inversine ; Mecamylamine ; Mecamylamine Hydrochloride ; 2-[Methylamino]Isocamphane Hydrochloride ; 3-Methylaminoisocamphanehydrochloride ; 3-Methylaminoisokamfanchlorid ; Inversinehydrochloride
Product Categories: Acetylcholine receptor
MF: C11H22ClN
MW: 203.75
EINECS: 212-555-8
Flash Point: 58.1 °C
Boiling Point: 189.3 °C at 760 mmHg
Vapour Pressure: 0.573 mmHg at 25°C
Enthalpy of Vaporization: 42.55 kJ/mol
Solubility ethanol: 122 mg/mL
Following is the molecular structure of Mevasin Hydrochloride (CAS NO.826-39-1) is:
Mecamylamine hydrochloride Uses
Mevasin Hydrochloride (CAS NO.826-39-1) has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool. It is also sometimes used as an anti-addictive drug to help people stop smoking tobacco, and is now more widely used for this application than it is for lowering blood pressure. This effect is thought to be due to it blocking α3β4 nicotinic receptors in the brain.
Mecamylamine hydrochloride Toxicity Data With Reference
| Organism | Test Type | Route | Reported Dose (Normalized Dose) | Effect | Source |
|---|---|---|---|---|---|
| guinea pig | LD50 | intraperitoneal | 63mg/kg (63mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956. | |
| guinea pig | LD50 | oral | 175mg/kg (175mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956. | |
| guinea pig | LD50 | subcutaneous | 155mg/kg (155mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956. | |
| mouse | LD50 | intraperitoneal | 17mg/kg (17mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970. | |
| mouse | LD50 | intravenous | 14mg/kg (14mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970. | |
| mouse | LD50 | oral | 92mg/kg (92mg/kg) | Drugs in Japan Vol. 6, Pg. 814, 1982. | |
| mouse | LD50 | subcutaneous | 81mg/kg (81mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970. | |
| rat | LD50 | intraperitoneal | 53mg/kg (53mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 301, 1970. | |
| rat | LD50 | intravenous | 21mg/kg (21mg/kg) | Research Progress in Organic-Biological and Medicinal Chemistry. Vol. 2, Pg. 300, 1970. | |
| rat | LD50 | oral | 208mg/kg (208mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956. | |
| rat | LD50 | subcutaneous | 177mg/kg (177mg/kg) | Journal of Pharmacology and Experimental Therapeutics. Vol. 117, Pg. 169, 1956. |
Mecamylamine hydrochloride Safety Profile
Poison by ingestion, intraperitoneal, intravenous, and subcutaneous routes. When heated to decomposition it emits very toxic fumes of HCl and NOx.
Hazard Codes:
Xn
Risk Statements:
R22:Harmful if swallowed.
R36/37/38:Irritating to eyes, respiratory system and skin.
Safety Statements:
S36/37/39:Wear suitable protective clothing, gloves and eye/face protection.
RIDADR: UN 2811 6.1/PG 3
WGK Germany: 3
RTECS: RB6900000
Mecamylamine hydrochloride Specification
Biochem/physiol actions is Noncompetitive nicotinic acetylcholine receptor antagonist; preferentially blocks nicotinic receptors at autonomic ganglia; crosses blood-brain barrier. Caution solutions are stable to autoclaving.
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