Identification
- Summary
Mecamylamine is a nicotine antagonist used to treat moderate to severe essential hypertension and uncomplicated malignant hypertension.
- Brand Names
- Inversine, Vecamyl
- Generic Name
- Mecamylamine
- DrugBank Accession Number
- DB00657
- Background
A nicotinic antagonist that is well absorbed from the gastrointestinal tract and crosses the blood-brain barrier. Mecamylamine has been used as a ganglionic blocker in treating hypertension, but, like most ganglionic blockers, is more often used now as a research tool.
- Type
- Small Molecule
- Groups
- Approved, Investigational
- Structure
Structure for Mecamylamine (DB00657)
- Weight
- Average: 167.2911
Monoisotopic: 167.167399677 - Chemical Formula
- C11H21N
- Synonyms
- Mecamylamine
Pharmacology
- Indication
For the treatment of moderately severe to severe essential hypertension and in uncomplicated cases of malignant hypertension
Reduce drug development failure ratesBuild, train, & validate machine-learning modelswith evidence-based and structured datasets.Build, train, & validate predictive machine-learning models with structured datasets.- Associated Conditions
Indication Type Indication Combined Product Details Approval Level Age Group Patient Characteristics Dose Form Management of Severe hypertension •••••••••••• Management of Moderate hypertension •••••••••••• Management of Uncomplicated malignant hypertension •••••••••••• - Contraindications & Blackbox Warnings
Prevent Adverse Drug Events TodayTap into our Clinical API for life-saving information on contraindications & blackbox warnings, population restrictions, harmful risks, & more.Avoid life-threatening adverse drug events with our Clinical API- 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.
Target Actions Organism ANeuronal acetylcholine receptor subunit alpha-2 antagonistHumans UNeuronal acetylcholine receptor subunit alpha-7 Not Available Humans UNeuronal acetylcholine receptor subunit alpha-4 Not Available Humans UNeuronal acetylcholine receptor subunit beta-2 Not Available Humans - Absorption
Mecamylamine is almost completely absorbed from the gastrointestinal tract
- Volume of distribution
Not Available
- Protein binding
40%
- Metabolism
- Not Available
- Route of elimination
Mecamylamine is excreted slowly in the urine in the unchanged form. The rate of its renal elimination is influenced markedly by urinary pH. Alkalinization of the urine reduces, and acidification promotes, renal excretion of mecamylamine. Mecamylamine crosses the blood-brain and placental barriers.
- Half-life
Not Available
- Clearance
Not Available
- Adverse Effects
Improve decision support & research outcomesWith structured adverse effects data, including: blackbox warnings, adverse reactions, warning & precautions, & incidence rates. View sample adverse effects data in our new Data Library!Improve decision support & research outcomes with our structured adverse effects data.- Toxicity
Not Available
- Pathways
- Not Available
- Pharmacogenomic Effects/ADRs Browse all" title="About SNP Mediated Effects/ADRs" id="snp-actions-info" class="drug-info-popup" href="javascript:void(0);">
- Not Available
Interactions
- Drug Interactions Learn More" title="About Drug Interactions" id="structured-interactions-info" class="drug-info-popup" href="javascript:void(0);">
- This information should not be interpreted without the help of a healthcare provider. If you believe you are experiencing an interaction, contact a healthcare provider immediately. The absence of an interaction does not necessarily mean no interactions exist.
Drug Interaction Integrate drug-drug
interactions in your softwareAbacavir Mecamylamine may decrease the excretion rate of Abacavir which could result in a higher serum level. Abaloparatide The risk or severity of adverse effects can be increased when Mecamylamine is combined with Abaloparatide. Acebutolol Mecamylamine may increase the hypotensive activities of Acebutolol. Aceclofenac The therapeutic efficacy of Mecamylamine can be decreased when used in combination with Aceclofenac. Acemetacin The therapeutic efficacy of Mecamylamine can be decreased when used in combination with Acemetacin. - Food Interactions
- Avoid excessive or chronic alcohol consumption. The ingestion of alcohol may potentiate the actions of mecamylamine.
- Take after a meal. This slows mecamylamine absorption allowing for a gradual reduction in blood pressure. Take consistently at the same time in regard to meals.
Products
Drug product information from 10+ global regionsOur datasets provide approved product information including:dosage, form, labeller, route of administration, and marketing period.Access drug product information from over 10 global regions.- Product Ingredients
Ingredient UNII CAS InChI Key Mecamylamine hydrochloride 4956DJR58O 826-39-1 PKVZBNCYEICAQP-UHFFFAOYSA-N - Brand Name Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Inversine Tablet 2.5 mg/1 Oral Targacept, Inc. 2006-07-25 Not applicable US 
- Generic Prescription Products
Name Dosage Strength Route Labeller Marketing Start Marketing End Region Image Mecamylamine Hydrochloride Tablet 2.5 mg/1 Oral LGM Pharma Solutions, LLC 2013-03-19 Not applicable US Mecamylamine Hydrochloride Tablet 2.5 mg/1 Oral Nexgen Pharma, Inc. 2013-03-19 Not applicable US Vecamyl Tablet 2.5 mg/1 Oral Vyera Pharmaceuticals, LLC 2013-03-19 Not applicable US Vecamyl Tablet 2.5 mg/1 Oral Manchester Pharmaceuticals 2013-03-19 Not applicable US
Categories
- ATC Codes
- C02BB01 — Mecamylamine
- Drug Categories
- Agents that produce neuromuscular block (indirect)
- Antiadrenergic Agents, Ganglion-Blocking
- Anticholinergic Agents
- Antihypertensive Agents
- Antihypertensive Agents Indicated for Hypertension
- Autonomic Agents
- Bridged-Ring Compounds
- Cardiovascular Agents
- Cholinergic Agents
- Decreased Autonomic Ganglionic Activity
- Drugs that are Mainly Renally Excreted
- Ganglion Blockers
- Hypotensive Agents
- Neurotransmitter Agents
- Nicotinic Antagonists
- Norbornanes
- Peripheral Nervous System Agents
- Secondary and Tertiary Amines
- Chemical TaxonomyProvided by Classyfire
- Description
- This compound belongs to the class of organic compounds known as bicyclic monoterpenoids. These are monoterpenoids containing exactly 2 rings, which are fused to each other.
- Kingdom
- Organic compounds
- Super Class
- Lipids and lipid-like molecules
- Class
- Prenol lipids
- Sub Class
- Monoterpenoids
- Direct Parent
- Bicyclic monoterpenoids
- Alternative Parents
- Dialkylamines / Organopnictogen compounds / Hydrocarbon derivatives
- Substituents
- Aliphatic homopolycyclic compound / Amine / Bicyclic monoterpenoid / Hydrocarbon derivative / Organic nitrogen compound / Organonitrogen compound / Organopnictogen compound / Secondary aliphatic amine / Secondary amine
- Molecular Framework
- Aliphatic homopolycyclic compounds
- External Descriptors
- primary aliphatic amine (CHEBI:6706)
- Affected organisms
- Humans and other mammals
Chemical Identifiers
- UNII
- Not Available
- CAS number
- 60-40-2
- InChI Key
- IMYZQPCYWPFTAG-UHFFFAOYSA-N
- InChI
- InChI=1S/C11H21N/c1-10(2)8-5-6-9(7-8)11(10,3)12-4/h8-9,12H,5-7H2,1-4H3
- IUPAC Name
- N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine
- SMILES
- CNC1(C)C2CCC(C2)C1(C)C
References
- Synthesis Reference
U.S. Patent 2,831,027.
- General References
- FDA Approved Drug Products: INVERSINE (mecamylamine hydrochloride) tablets [Link]
- External Links
- Human Metabolome Database
- HMDB0014795
- KEGG Compound
- C07511
- PubChem Compound
- 4032
- PubChem Substance
- 46508607
- ChemSpider
- 3892
- BindingDB
- 50061565
- 6673
- ChEBI
- 6706
- ChEMBL
- CHEMBL267936
- Therapeutic Targets Database
- DAP000027
- PharmGKB
- PA450334
- Guide to Pharmacology
- GtP Drug Page
- RxList
- RxList Drug Page
- Drugs.com
- Drugs.com Drug Page
- Wikipedia
- Mecamylamine
Clinical Trials
- Clinical Trials Learn More" title="About Clinical Trials" id="clinical-trials-info" class="drug-info-popup" href="javascript:void(0);">
Phase Status Purpose Conditions Count 4 Unknown Status Prevention Spinal Cord Injuries 1 3 Completed Treatment Alcohol Dependency / Depression 1 2 Completed Treatment Age - Related Macular Degeneration (AMD) 1 2 Completed Treatment Alcohol Dependency 1 2 Completed Treatment Depression / Major Depressive Disorder (MDD) 1
Pharmacoeconomics
- Manufacturers
- Targacept inc
- Packagers
- Layton Bioscience Inc.
- Siegfried Ltd.
- Dosage Forms
Form Route Strength Tablet Oral 2.5 mg/1 - Prices
- Not Available
- Patents
- Not Available
Properties
- State
- Liquid
- Experimental Properties
Property Value Source melting point (°C) 249 with decomposition U.S. Patent 2,831,027. boiling point (°C) 72 °C at 4.00E+00 mm Hg PhysProp logP 2.7 Not Available - Predicted Properties
Property Value Source Water Solubility 0.124 mg/mL ALOGPS logP 3.13 ALOGPS logP 2.37 Chemaxon logS -3.1 ALOGPS pKa (Strongest Basic) 10.88 Chemaxon Physiological Charge 1 Chemaxon Hydrogen Acceptor Count 1 Chemaxon Hydrogen Donor Count 1 Chemaxon Polar Surface Area 12.03 Å2 Chemaxon Rotatable Bond Count 1 Chemaxon Refractivity 51.83 m3·mol-1 Chemaxon Polarizability 20.74 Å3 Chemaxon Number of Rings 2 Chemaxon Bioavailability 1 Chemaxon Rule of Five Yes Chemaxon Ghose Filter Yes Chemaxon Veber's Rule Yes Chemaxon MDDR-like Rule No Chemaxon - Predicted ADMET Features
Property Value Probability Human Intestinal Absorption + 0.9566 Blood Brain Barrier + 0.9771 Caco-2 permeable + 0.611 P-glycoprotein substrate Non-substrate 0.6815 P-glycoprotein inhibitor I Non-inhibitor 0.8271 P-glycoprotein inhibitor II Non-inhibitor 0.889 Renal organic cation transporter Non-inhibitor 0.7727 CYP450 2C9 substrate Non-substrate 0.7864 CYP450 2D6 substrate Non-substrate 0.7207 CYP450 3A4 substrate Substrate 0.5884 CYP450 1A2 substrate Non-inhibitor 0.9046 CYP450 2C9 inhibitor Non-inhibitor 0.907 CYP450 2D6 inhibitor Non-inhibitor 0.9231 CYP450 2C19 inhibitor Non-inhibitor 0.9026 CYP450 3A4 inhibitor Non-inhibitor 0.9054 CYP450 inhibitory promiscuity Low CYP Inhibitory Promiscuity 0.7435 Ames test Non AMES toxic 0.9315 Carcinogenicity Non-carcinogens 0.8757 Biodegradation Not ready biodegradable 0.6954 Rat acute toxicity 2.3843 LD50, mol/kg Not applicable hERG inhibition (predictor I) Weak inhibitor 0.9676 hERG inhibition (predictor II) Non-inhibitor 0.8756
Spectra
- Mass Spec (NIST)
- Not Available
- Spectra
- Chromatographic Properties
Collision Cross Sections (CCS)
Adduct CCS Value (Å2) Source type Source [M-H]- 137.4495272 predictedDarkChem Lite v0.1.0 [M-H]- 139.21428 predictedDeepCCS 1.0 (2019) [M+H]+ 137.4685272 predictedDarkChem Lite v0.1.0 [M+H]+ 141.98457 predictedDeepCCS 1.0 (2019) [M+Na]+ 137.4030272 predictedDarkChem Lite v0.1.0 [M+Na]+ 150.75584 predictedDeepCCS 1.0 (2019)
Targets
Build, predict & validate machine-learning models
Use our structured and evidence-based datasets to unlock newinsights and accelerate drug research.
Use our structured and evidence-based datasets to unlock new insights and accelerate drug research.
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Yes
- Actions
- Antagonist
- General Function
- Drug binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane.
- Gene Name
- CHRNA2
- Uniprot ID
- Q15822
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-2
- Molecular Weight
- 59764.82 Da
References
- Overington JP, Al-Lazikani B, Hopkins AL: How many drug targets are there? Nat Rev Drug Discov. 2006 Dec;5(12):993-6. [Article]
- Imming P, Sinning C, Meyer A: Drugs, their targets and the nature and number of drug targets. Nat Rev Drug Discov. 2006 Oct;5(10):821-34. [Article]
- Chen X, Ji ZL, Chen YZ: TTD: Therapeutic Target Database. Nucleic Acids Res. 2002 Jan 1;30(1):412-5. [Article]
- Struthers AM, Wilkinson JL, Dwoskin LP, Crooks PA, Bevins RA: Mecamylamine, dihydro-beta-erythroidine, and dextromethorphan block conditioned responding evoked by the conditional stimulus effects of nicotine. Pharmacol Biochem Behav. 2009 Dec;94(2):319-28. doi: 10.1016/j.pbb.2009.09.012. Epub 2009 Sep 22. [Article]
- Shytle RD, Penny E, Silver AA, Goldman J, Sanberg PR: Mecamylamine (Inversine): an old antihypertensive with new research directions. J Hum Hypertens. 2002 Jul;16(7):453-7. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- General Function
- Toxic substance binding
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane. The cha...
- Gene Name
- CHRNA7
- Uniprot ID
- P36544
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-7
- Molecular Weight
- 56448.925 Da
References
- Briggs CA, McKenna DG, Monteggia LM, Touma E, Roch JM, Arneric SP, Gopalakrishnan M, Sullivan JP: Gain of function mutation of the alpha7 nicotinic receptor: distinct pharmacology of the human alpha7V274T variant. Eur J Pharmacol. 1999 Feb 5;366(2-3):301-8. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- noncompetitive antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
- Gene Name
- CHRNA4
- Uniprot ID
- P43681
- Uniprot Name
- Neuronal acetylcholine receptor subunit alpha-4
- Molecular Weight
- 69956.47 Da
References
- Eaton JB, Peng JH, Schroeder KM, George AA, Fryer JD, Krishnan C, Buhlman L, Kuo YP, Steinlein O, Lukas RJ: Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. Mol Pharmacol. 2003 Dec;64(6):1283-94. [Article]
- Kind
- Protein
- Organism
- Humans
- Pharmacological action
- Unknown
- Curator comments
- noncompetitive antagonist
- General Function
- Ligand-gated ion channel activity
- Specific Function
- After binding acetylcholine, the AChR responds by an extensive change in conformation that affects all subunits and leads to opening of an ion-conducting channel across the plasma membrane permeabl...
- Gene Name
- CHRNB2
- Uniprot ID
- P17787
- Uniprot Name
- Neuronal acetylcholine receptor subunit beta-2
- Molecular Weight
- 57018.575 Da
References
- Eaton JB, Peng JH, Schroeder KM, George AA, Fryer JD, Krishnan C, Buhlman L, Kuo YP, Steinlein O, Lukas RJ: Characterization of human alpha 4 beta 2-nicotinic acetylcholine receptors stably and heterologously expressed in native nicotinic receptor-null SH-EP1 human epithelial cells. Mol Pharmacol. 2003 Dec;64(6):1283-94. [Article]
Drug created at June 13, 2005 13:24 / Updated at December 02, 2023 06:53