Mecamylamine Hydrochloride
Basic information
- CAS
826-39-1- Standard SMILES
CNC1(C)C2CCC(C2)C1(C)C.Cl- InChIKey
PKVZBNCYEICAQP-UHFFFAOYSA-N- Molecular formula
- C11H22ClN
- Average molar mass
- 203.75 g/mol
- Monoisotopic mass
- 203.1440774
Overview
Mecamylamine hydrochloride is a monoterpenoid.
Names & identifiers
- Preferred name
- Mecamylamine Hydrochloride
- IUPAC
- N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine;hydrochloride
- English name
- Mecamylamine hydrochloride
- Molecular formula
- C11H22ClN
- Molecular weight
- 203.75
Names & synonyms
MECAMYLAMINE HYDROCHLORIDE826-39-1InversineMevasinVecamylMekamin hydrochlorideMecamine hydrochlorideMecamylamine HCl3-Methylaminoisokamfan chlorid3-Methylaminoisocamphane hydrochlorideN-Methyl-dl-isobornylamine hydrochlorideCPDB 0059
Show more names
MECAMYLAMINEMECAMYLAMINE USPMecaMycaMine HClMECAMYLAMINE USPmevasinhydrochloridemekaminhydrochloridemecaminehydrochloride
EINECS 212-555-8UNII-4956DJR58ONSC-7570862-Norbornanamine, N,2,3,3-tetramethyl-, hydrochlorideMecamylamine hydrochloride (USP)Mecamylamine hydrochloride [USP]4956DJR58ON-Methyl-N-2,5-endomethylene-1,6,6-trimethylcyclohexylamine hydrochloride
Database identifiers
- CAS
826-39-1- PubChem CID
- 13221
- DTXSID
DTXSID70896795- ChEMBL
CHEMBL1237082- ChEBI
CHEBI:6707- EC Number
- 212-555-8
Properties
Computed structural properties
- Topological polar surface area
- 12 Ų
- Hydrogen bond donors
- 2
- Hydrogen bond acceptors
- 1
- Rotatable bonds
- 1
- Heavy atoms
- 13
- Formal charge
- 0
- Complexity
- 197
Experimental & physicochemical properties
Human Drugs
FDA approved drugs -> Active ingredient
FDA approved drugs -> Active ingredient
Physicochemical properties
- Melting point
- 240 °C · >240°C (dec.)
- storage temp.
- 2 · 2-8°C
- solubility
- 122 mg/mL · ethanol: 122 mg/mL
- pka
- 11.2 · pKa 11.2(H2O,t undefined,I=0.1) (Uncertain)
- form
- Solid
- color
- White to off-white
- Water Solubility
- 2 O: · H2O: 100mM
- Stability
- Hygroscopic
- Major Application
- pharmaceutical (small molecule)
- InChI
- InChI=1/C11H21N.ClH/c1-10(2)8-5-6-9(7-8)11(10,3)12-4;/h8-9,12H,5-7H2,1-4H3;1H/t8-,9+,11;/s3
- InChIKey
- PKVZBNCYEICAQP-YENZGJFJNA-N
- SMILES
- C1(C)(NC)C(C)(C)[C@]2([H])CC[C@@]1([H])C2.Cl |&1:7,11,r|
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
Danger
H301 (97.6%): Toxic if swallowed [Danger Acute toxicity, oral]
P261, P264, P264+P265, P270, P271, P280, P301+P316, P302+P352, P304+P340, P305+P351+P338, P319, P321, P330, P332+P317, P337+P317, P362+P364, P403+P233, P405, and P501 (click each P-code to see the statement)
Aggregated GHS information provided per 42 reports by companies from 4 notifications to the ECHA C&L Inventory. Each notification may be associated with multiple companies.
Hazard information
Regulatory InformationBicyclo2.2.1heptan-2-amine, N,2,3,3-tetramethyl-, hydrochloride: Does not have an individual approval but may be used as a component in a product covered by a group standard. It is not approved for use as a chemical in its own right.
Hazard Classes and CategoriesAcute Tox. 3 (97.6%)
Toxicology
Drug Induced Liver Injury
Drug Induced Liver Injury Rank (DILIrank 2.0)
Mecamylamine hydrochloride
vNo-DILI-concern
0
No match
DOI:10.1016/j.drudis.2016.02.015
Safety data
- wgk
- 3
- rtecs
- RB6900000
- ridadr
- UN 2811 6.1/PG 3
- hs_code
- 2921300000
- risk_code
- 22-36/37/38
- Signal word
- Danger
Chemistry & industry
Pharmacology
FDA Pharmacological Classification
MECAMYLAMINE HYDROCHLORIDE
Decreased Autonomic Ganglionic Activity [PE]; Autonomic Ganglionic Blocker [EPC]
Applications
DescriptionMecamylamine hydrochloride is a non-competitive nicotinic acetylcholine receptor antagonist with preferential activity at the α3β4 subtype (IC50 = 90-640 nM) compared to α4β2, α3β2, and α7 subtypes (IC50 range from 1-7 μM), previously used to treat hypertension.Displays antidepressant-like effects in mice.Mecamylamine HCl is supplied as tablets for oral use, each containing 2.5 mg mecamylamine HCl. Inactive ingredients are calcium phosphate, D&C Yellow 10, FD&C Yellow 6, lactose, magnesium stearate, cornstarch, and talc.
UsesMecamylamine hydrochloride has been used as an additive in extracellular saline during current-clamp recordings to reduce synaptic input. It has also been used as a non-selective nicotinic acetyl choline receptor blocker in aortic body neurons and in MLO-Y4 cells.
UsesMecamylamine is a noncompetitive nicotinic acetylcholine receptor antagonist with preferential activity at the α3β4 subtype (IC50 = 90-640 nM) compared to α4β2, α3β2, and α7 subtypes (IC50s range from 1-7 μM). Mecamylamine is widely used as a broad-spectrum antagonist of neuronal nicotinic acetylcholine receptors in basic nicotine research. It has been reported to be effective as an aid to smoking cessation and may also be of use in various nicotine-responsive, neuropsychiatric disorders.[Cayman Chemical]
UsesA noncompetitive nicotinic AChR inhibitor.
UsesCurrently, mecamylamine is the only ganglioblocker used for general hypertension; however, the need has declined because of the possibility of addiction and the introduction of many other antihypertensive drugs into medical practice.
General DescriptionThe secondary aminemecamylamine hydrochloride, N,2,3,3-tetramethyl-2-norbornanaminehydrochloride (Inversine), has a powerful ganglionicblocking effect that is almost identical to that ofhexamethonium. It has an advantage over most of the ganglionicblocking agents in being absorbed readily andsmoothly from the GI tract. It is rarely used, however, forthe treatment of moderate-to-severe hypertension becausesevere orthostatic hypotension occurs when the drug blockssympathetic ganglia.
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