methyl(2,3,3-trimethyltrinorbornan-2-yl)amine

Modify Date: 2024-01-06 19:55:56

methyl(2,3,3-trimethyltrinorbornan-2-yl)amine structure	Common Name	methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
	CAS Number	60-40-2	Molecular Weight	167.29100
	Density	0.91	Boiling Point	189.3ºC at 760 mmHg
	Molecular Formula	C₁₁H₂₁N	Melting Point	245-256ºC
	MSDS	N/A	Flash Point	58.1ºC

Use of methyl(2,3,3-trimethyltrinorbornan-2-yl)amine

Mecamylamine is an orally active, nonselective, noncompetitive nAChR antagonist. Mecamylamine is also a ganglionic blocker. Mecamylamine can across the blood-brain barrier. Mecamylamine can be used in the research of neuropsychiatric disorders, hypertension, antidepressant area[1][2][5].

Name	N,2,2,3-tetramethylbicyclo[2.2.1]heptan-3-amine
Synonym	More Synonyms

Description	Mecamylamine is an orally active, nonselective, noncompetitive nAChR antagonist. Mecamylamine is also a ganglionic blocker. Mecamylamine can across the blood-brain barrier. Mecamylamine can be used in the research of neuropsychiatric disorders, hypertension, antidepressant area[1][2][5].
Related Catalog	Research Areas >> Cardiovascular Disease Signaling Pathways >> Immunology/Inflammation >> Histamine Receptor Signaling Pathways >> Membrane Transporter/Ion Channel >> nAChR Signaling Pathways >> Neuronal Signaling >> nAChR Research Areas >> Neurological Disease Signaling Pathways >> GPCR/G Protein >> Histamine Receptor
Target	nAChR[1], histamine receptor[2]
In Vitro	Mecamylamine (0.5-9 μM, bath administered) increases the firing frequency of identified 5-HT DRN neurons[1]. Mecamylamine (0.5-9 μM, bath administered) increases the glutamatergic and decreases the GABAergic input of 5-HT DRN neurons[1]. Mecamylamine (1 mM, 5 min) blocks the histamine receptor and the histamine-induced contractions in helically cut strips of rabbit aorta[2]. Mecamylamine (10 μM,48 h) attenuates the effect of nicotine’s action of neuroprotection[3]. Mecamylamine (1-100 nM, 30 min) dose-dependently attenuates endothelial tube formation in HDMVECs[4]. Western Blot Analysis[3] Cell Line: [3] Concentration: 10 μM Incubation Time: 48 h Result: Reduced the nicotine-facilitated increase in ERK1/2.
In Vivo	Mecamylamine (subcutaneous pumps, 50 mg/kg/day, 2 days) inhibits Choroidal neovascularization (CNV) in CNV mice model[4]. Mecamylamine (intraperitoneal injection, 0.5-1 mg/kg) has antidepressant-like effects in both the TST (tail suspension test) and FST (forced swim test) in C57BL/6J mice, which are dependent on bothβ2 andα7 subunits[5]. Animal Model: Choroidal neovascularization (CNV) mice model[1] Dosage: 50 mg/kg/day, 2 days Administration: Subcutaneous pumps implanted beneath the skin of the back), 200 μL and mean pumping rate of 0.5 μL/h. Result: Suppressed the development of CNV at Bruch’s membrane rupture sites in the absence of nicotine. Animal Model: C57BL/6J mice[5] Dosage: 0.5-1 mg/kg Administration: Intraperitoneal injection Result: Had no effect in β2 knockout miceand α7 knockout mice, but decreased immobility time in wildtype littermates in the FST.
References	[1]. Omar Hernández-González, et al. Mechanisms of stimulatory effects of mecamylamine on the dorsal raphe neurons. Brain Res Bull. 2020 Nov;164:289-298. [2]. C P Robinson, et al. The influence of mecamylamine on contractions induced by different agonists and on the role of calcium ions in the isolated rabbit aorta. J Pharmacol Exp Ther. 1976 Apr;197(1):57-65. [3]. Mahadevappa P Badanavalu, et al. Nicotine is neuroprotective to neonatal neurons of sympathetic ganglion in rat. Auton Neurosci. 2019 Jan;216:25-32. [4]. Katsuji Kiuchi, et al. Mecamylamine suppresses Basal and nicotine-stimulated choroidal neovascularization. Invest Ophthalmol Vis Sci. 2008 Apr;49(4):1705-11. [5]. 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.

Density	0.91
Boiling Point	189.3ºC at 760 mmHg
Melting Point	245-256ºC
Molecular Formula	C₁₁H₂₁N
Molecular Weight	167.29100
Flash Point	58.1ºC
Exact Mass	167.16700
PSA	12.03000
LogP	2.81150
Index of Refraction	1.4875

CHEMICAL IDENTIFICATION

RTECS NUMBER :: RB6880000

CHEMICAL NAME :: 2-Norbornanamine, N,2,3,3-tetramethyl-

CAS REGISTRY NUMBER :: 60-40-2

LAST UPDATED :: 199703

DATA ITEMS CITED :: 4

MOLECULAR FORMULA :: C11-H21-N

MOLECULAR WEIGHT :: 167.33

WISWESSER LINE NOTATION :: L55 ATJ CM1 C1 D1 D1

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Oral

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 90 mg/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: BCFAAI Bollettino Chimico Farmaceutico. (Societa Editoriale Farmaceutica, Via Ausonio 12, 20123 Milan, Italy) V.33- 1894- Volume(issue)/page/year: 103,490,1964

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intraperitoneal

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 40 mg/kg

TOXIC EFFECTS :: Behavioral - sleep

REFERENCE :: AITEAT Archivum Immunologiae et Therapiae Experimentalis. (Ars Polona, POB 1001, 00-068 Warsaw 1, Poland) V.10- 1962- Volume(issue)/page/year: 10,905,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Subcutaneous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 37500 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: FATOAO Farmakologiya i Toksikologiya (Moscow). For English translation, see PHTXA6 and RPTOAN. (V/O Mezhdunarodnaya Kniga, 113095 Moscow, USSR) V.2- 1939- Volume(issue)/page/year: 25,163,1962

TYPE OF TEST :: LD50 - Lethal dose, 50 percent kill

ROUTE OF EXPOSURE :: Intravenous

SPECIES OBSERVED :: Rodent - mouse

DOSE/DURATION :: 11900 ug/kg

TOXIC EFFECTS :: Details of toxic effects not reported other than lethal dose value

REFERENCE :: USXXAM United States Patent Document. (U.S. Patent Office, Box 9, Washington, DC 20231) Volume(issue)/page/year: #4168308

EINECS 200-476-1

Dayang Chem (Hangzhou) Co., Ltd.
China
Product Name: mecamylamine
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Purity: 98.0%
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Use of methyl(2,3,3-trimethyltrinorbornan-2-yl)amine

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Biological Activity

Chemical & Physical Properties

Toxicological Information

CHEMICAL IDENTIFICATION

HEALTH HAZARD DATA

ACUTE TOXICITY DATA

Synonyms