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60-40-2

60-40-2 structure
60-40-2 structure
  • Name: methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
  • Chemical Name: N,2,2,3-tetramethylbicyclo[2.2.1]heptan-3-amine
  • CAS Number: 60-40-2
  • Molecular Formula: C11H21N
  • Molecular Weight: 167.29100
  • Catalog: Pharmaceutical intermediate Heterocyclic compound Pyridine compound Bromopyridine
  • Create Date: 2018-07-30 21:27:17
  • Modify Date: 2024-01-06 19:55:56
  • 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
Synonyms EINECS 200-476-1
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
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

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