Basic information
- CAS
60-40-2- Standard SMILES
CNC1(C)C2CCC(C2)C1(C)C- InChIKey
IMYZQPCYWPFTAG-UHFFFAOYSA-N- Molecular formula
- C11H21N
- Average molar mass
- 167.29 g/mol
- Monoisotopic mass
- 167.16739967
Overview
Mecamylamine is a primary aliphatic amine.
Names & identifiers
- Preferred name
- Mecamylamine
- IUPAC
- N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
- English name
- methyl(2,3,3-trimethyltrinorbornan-2-yl)amine
- Molecular formula
- C11H21N
- Molecular weight
- 167.29
Names & synonyms
mecamylamineVersamine60-40-2MecamilaminaN,2,3,3-Tetramethylbicyclo[2.2.1]heptan-2-amineMecamylaminumDTXSID0023240Bicyclo(2.2.1)heptan-2-amine, N,2,3,3-tetramethyl-DTXCID903240Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl-N,2,3,3-tetramethylbicyclo(2.2.1)heptan-2-amineRefChem:56912
Show more names
MevasineRevetinaPleganginMECAMYLAMINE BASEN-Methyl-2-isocamphanamineN,2,3,3-Tetramethyl-2-norcamphanamine
C02BB01200-476-1(1RS,2SR,4SR)-N,2,3,3-Tetramethylbicyclo(2.2.1)heptan-2-amine6EE945D3OKN,2,3,3-Tetramethyl-2-norbornanamineRevertinaMecamineMekamine
Database identifiers
- CAS
60-40-2- PubChem CID
- 4032
- DTXSID
DTXSID0023240- ChEMBL
CHEMBL267936
Properties
Computed structural properties
- XLogP
- 2.6
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 1
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 12
- Formal charge
- 0
- Complexity
- 197
Experimental & physicochemical properties
LogP2.7
Solubility1.24e-01 g/L
Human DrugsPharmaceuticals
Melting Point< 25 °C
Physical DescriptionSolid
Physicochemical properties
- Melting point
- 245 · 245-256℃
- Boiling point
- 189 ℃ · 189℃
- Density
- 0.91 · 0.91
- refractive index
- 1.4875 · 1.4875
- Flash point
- 58 ℃ · 58℃
- FDA UNII
- 6 EE945D3OK · 6EE945D3OK
- EPA Substance Registry System
- 2.2 · Bicyclo[2.2.1]heptan-2-amine, N,2,3,3-tetramethyl- (60-40-2)
- Symbol(GHS)
- 7 · GHS07
- Signal word
- Warning
Safety & regulation
Safety information is for reference only and does not replace the supplier’s Safety Data Sheet (SDS), applicable regulations, or professional assessment.
GHS classification
GHS Classification
Warning
H302 (100%): Harmful if swallowed [Warning Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P317, P302+P352, P304+P340, P305+P351+P338, P317, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
The GHS information provided by 1 company from 1 notification to the ECHA C&L Inventory.
Hazard information
Hazard Classes and CategoriesAcute Tox. 4 (100%)
Toxicology
Drug Induced Liver Injury
Drug-Induced Liver Injury Severity and Toxicity (DILIst)
mecamylamine
DILI Negative
Oral
DOI:10.1016/j.drudis.2019.09.022
Safety data
- Signal word
- Warning
- Symbol(GHS)
- GHS07
- Hazard statements
- H312-H319-H302-H332-H335-H315
- Precautionary statements
- P264-P280-P302+P352-P321-P332+P313-P362-P280-P302+P352-P312-P322-P363-P501-P264-P270-P301+P312-P330-P501-P261-P271-P304+P340-P312-P264-P280-P305+P351+P338-P337+P313P
Chemistry & industry
Pharmacology
ATC Code
C - Cardiovascular system
QC - Cardiovascular system
Protein Binding40%
Pharmacodynamics
Mecamylamine is a potent, oral antihypertensive agent and ganglion blocker, and is a secondary amine. Mecamylamine is indicated for the management of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension. Mecamylamine reduces blood pressure in both normotensive and hypertensive individuals. A small oral dosage often produces a smooth and predictable reduction of blood pressure. Although this antihypertensive effect is predominantly orthostatic, the supine blood pressure is also significantly reduced. Mecamylamine crosses the blood-brain and placental barriers.
Mechanism of Action
Mecamylamine is a ganglionic blocker which prevents stimulation of postsynaptic receptors by acetylcholine released from presynaptic nerve endings. The hypotensive effect of Mecamylamine is attributed to reduction in sympathetic tone, vasodilation, and reduced cardiac output, and is primarily postural.
FDA Pharmacological Classification
6EE945D3OK
MECAMYLAMINE
Established Pharmacologic Class [EPC] - Autonomic Ganglionic Blocker
Physiologic Effects [PE] - Decreased Autonomic Ganglionic Activity
Mecamylamine is an Autonomic Ganglionic Blocker. The physiologic effect of mecamylamine is by means of Decreased Autonomic Ganglionic Activity.
MeSH Pharmacological Classification
Drugs used in the treatment of acute or chronic vascular HYPERTENSION regardless of pharmacological mechanism. Among the antihypertensive agents are DIURETICS; (especially DIURETICS, THIAZIDE); ADRENERGIC BETA-ANTAGONISTS; ADRENERGIC ALPHA-ANTAGONISTS; ANGIOTENSIN-CONVERTING ENZYME INHIBITORS; CALCIUM CHANNEL BLOCKERS; GANGLIONIC BLOCKERS; and VASODILATOR AGENTS.
Agents having as their major action the interruption of neural transmission at nicotinic receptors on postganglionic autonomic neurons. Because their actions are so broad, including blocking of sympathetic and parasympathetic systems, their therapeutic use has been largely supplanted by more specific drugs. They may still be used in the control of blood pressure in patients with acute dissecting aortic aneurysm and for the induction of hypotension in surgery.
Related reactions
1 records
Compound notes
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