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MedKoo Cat#: 540282 | Name: Mecamylamine HCl
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Description:

WARNING: This product is for research use only, not for human or veterinary use.

Mecamylamine hydrochloride is a nAChR antagonist previously used to treat hypertension. It displays a wide variety of activities, including reducing depression-like behaviors in subjects with Tourette's syndrome and improving rates of smoking cessation.

Chemical Structure

Mecamylamine HCl
Mecamylamine HCl
CAS#826-39-1 (HCl)

Theoretical Analysis

MedKoo Cat#: 540282

Name: Mecamylamine HCl

CAS#: 826-39-1 (HCl)

Chemical Formula: C11H22ClN

Exact Mass: 203.1441

Molecular Weight: 203.75

Elemental Analysis: C, 64.84; H, 10.88; Cl, 17.40; N, 6.87

Price and Availability

Size Price Availability Quantity
250mg USD 350.00 2 Weeks
1g USD 750.00 2 Weeks
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Related CAS #
826-39-1 (HCl) 60-40-2 (free base)
Synonym
Inversine; Mecamine hydrochloride; Mecamylamine HCl; Mevasin;
IUPAC/Chemical Name
N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine hydrochloride
InChi Key
PKVZBNCYEICAQP-UHFFFAOYSA-N
InChi Code
InChI=1S/C11H21N.ClH/c1-10(2)8-5-6-9(7-8)11(10,3)12-4;/h8-9,12H,5-7H2,1-4H3;1H
SMILES Code
CC1(C)C(NC)(C)C2CCC1C2.[H]Cl
Appearance
Solid powder
Purity
>96% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>2 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info
Product Data
Product Data
Instruction
View handling instruction
Biological target:
Mecamylamine hydrochloride is an orally active, nonselective, noncompetitive nAChR antagonist.
In vitro activity:
Several nAChR isoforms were identified in retinal and choroidal microvascular endothelial cells, and the ability of these cells to form tubules when grown in growth factor-reduced basement membrane matrix and supplemented with VEGF was suppressed by the nAChR antagonist mecamylamine. Reference: Invest Ophthalmol Vis Sci. 2008 Apr;49(4):1705-11. https://pubmed.ncbi.nlm.nih.gov/18385094/
In vivo activity:
The exposure of helically cut strips of rabbit aorta to mecamylamine (1 mM) for 5 minutes blocked the histamine (3.25 muM)-induced contractions completely and reduced those induced by potassium (25mM, 68%) without affecting contractions induced by norepinephrine (3.0 muM, NE) or acetylcholine (10 muM). Mecamylamine in low doses (1 mM) blocks the histamine receptor and therefore the histamine-induced contractions. Mecamylamine in high doses (10 mM) partially blocks norepinephrine-induced contractions by affecting firmly bound calcium stores. Reference: J Pharmacol Exp Ther. 1976 Apr;197(1):57-65. https://pubmed.ncbi.nlm.nih.gov/1263133/
Solvent mg/mL mM
Solubility
DMF 2.0 9.82
DMSO 18.1 88.96
Ethanol 20.0 98.16
PBS (pH 7.2) 5.0 24.54
Water 100.0 490.79
Note: There can be variations in solubility for the same chemical from different vendors or different batches from the same vendor. The following factors can affect the solubility of the same chemical: solvent used for crystallization, residual solvent content, polymorphism, salt versus free form, degree of hydration, solvent temperature. Please use the solubility data as a reference only. Warming and sonication will facilitate dissolving. Still have questions? Please contact our Technical Support scientists.

Preparing Stock Solutions

The following data is based on the product molecular weight 203.75 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
Formulation protocol:
1. Hernández-González O, Mondragón-García A, Hernández-López S, Castillo-Rolon DE, Arenas-López G, Tapia D, Mihailescu S. Mechanisms of stimulatory effects of mecamylamine on the dorsal raphe neurons. Brain Res Bull. 2020 Nov;164:289-298. doi: 10.1016/j.brainresbull.2020.08.031. Epub 2020 Sep 7. PMID: 32910991. 2. Kiuchi K, Matsuoka M, Wu JC, Lima e Silva R, Kengatharan M, Verghese M, Ueno S, Yokoi K, Khu NH, Cooke JP, Campochiaro PA. Mecamylamine suppresses Basal and nicotine-stimulated choroidal neovascularization. Invest Ophthalmol Vis Sci. 2008 Apr;49(4):1705-11. doi: 10.1167/iovs.07-0089. PMID: 18385094; PMCID: PMC2636721. 3. Rabenstein RL, Caldarone BJ, Picciotto MR. 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. doi: 10.1007/s00213-006-0568-z. Epub 2006 Oct 3. PMID: 17016705. 4. Robinson CP, Sastry BV. 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. PMID: 1263133.
In vitro protocol:
1. Hernández-González O, Mondragón-García A, Hernández-López S, Castillo-Rolon DE, Arenas-López G, Tapia D, Mihailescu S. Mechanisms of stimulatory effects of mecamylamine on the dorsal raphe neurons. Brain Res Bull. 2020 Nov;164:289-298. doi: 10.1016/j.brainresbull.2020.08.031. Epub 2020 Sep 7. PMID: 32910991. 2. Kiuchi K, Matsuoka M, Wu JC, Lima e Silva R, Kengatharan M, Verghese M, Ueno S, Yokoi K, Khu NH, Cooke JP, Campochiaro PA. Mecamylamine suppresses Basal and nicotine-stimulated choroidal neovascularization. Invest Ophthalmol Vis Sci. 2008 Apr;49(4):1705-11. doi: 10.1167/iovs.07-0089. PMID: 18385094; PMCID: PMC2636721.
In vivo protocol:
1. Rabenstein RL, Caldarone BJ, Picciotto MR. 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. doi: 10.1007/s00213-006-0568-z. Epub 2006 Oct 3. PMID: 17016705. 2. Robinson CP, Sastry BV. 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. PMID: 1263133.
1: Nickell JR, Grinevich VP, Siripurapu KB, Smith AM, Dwoskin LP. Potential therapeutic uses of mecamylamine and its stereoisomers. Pharmacol Biochem Behav. 2013 Jul;108:28-43. doi: 10.1016/j.pbb.2013.04.005. Epub 2013 Apr 18. Review. PubMed PMID: 23603417; PubMed Central PMCID: PMC3690754. 2: Kirshenbaum AP, Jackson ER, Brown SJ, Fuchs JR, Miltner BC, Doughty AH. Nicotine-induced impulsive action: sensitization and attenuation by mecamylamine. Behav Pharmacol. 2011 Jun;22(3):207-21. doi: 10.1097/FBP.0b013e328345ca1c. PubMed PMID: 21448062; PubMed Central PMCID: PMC3151674. 3: Elrashidi MY, Ebbert JO. Emerging drugs for the treatment of tobacco dependence: 2014 update. Expert Opin Emerg Drugs. 2014 Jun;19(2):243-60. doi: 10.1517/14728214.2014.899580. Epub 2014 Mar 22. Review. PubMed PMID: 24654737. 4: Young JM, Shytle RD, Sanberg PR, George TP. Mecamylamine: new therapeutic uses and toxicity/risk profile. Clin Ther. 2001 Apr;23(4):532-65. Review. PubMed PMID: 11354389. 5: MECAMYLAMINE hydrochloride. J Am Med Assoc. 1956 Dec 15;162(16):1469-71. PubMed PMID: 13376320. 6: MUNSTER AM. The side effects of mecamylamine hydrochloride: a review of 50 cases. Med J Aust. 1961 Feb 18;48(1):247-9. PubMed PMID: 13726855. 7: Rose JE, Behm FM, Westman EC. Acute effects of nicotine and mecamylamine on tobacco withdrawal symptoms, cigarette reward and ad lib smoking. Pharmacol Biochem Behav. 2001 Feb;68(2):187-97. PubMed PMID: 11267622. 8: Suchocki JA, May EL, Martin TJ, George C, Martin BR. Synthesis of 2-exo- and 2-endo-mecamylamine analogues. Structure-activity relationships for nicotinic antagonism in the central nervous system. J Med Chem. 1991 Mar;34(3):1003-10. PubMed PMID: 2002445. 9: DATEY KK, JOSHI NK. Mecamylamine hydrochloride in the treatment of hypertension. J Indian Med Assoc. 1958 Jan 16;30(2):43-50. PubMed PMID: 13514093. 10: Buoli M, Serati M, Cahn W. Alternative pharmacological strategies for adult ADHD treatment: a systematic review. Expert Rev Neurother. 2016;16(2):131-44. doi: 10.1586/14737175.2016.1135735. Epub 2016 Jan 14. Review. PubMed PMID: 26693882. 11: Miyauchi M, Neugebauer NM, Oyamada Y, Meltzer HY. Nicotinic receptors and lurasidone-mediated reversal of phencyclidine-induced deficit in novel object recognition. Behav Brain Res. 2016 Mar 15;301:204-12. doi: 10.1016/j.bbr.2015.10.044. Epub 2015 Oct 28. PubMed PMID: 26519556. 12: Yousofizadeh S, Tamaddonfard E, Farshid AA. The role of nicotinic acetylcholine and opioid systems of the ventral orbital cortex in modulation of formalin-induced orofacial pain in rats. Eur J Pharmacol. 2015 Jul 5;758:147-52. doi: 10.1016/j.ejphar.2015.04.002. Epub 2015 Apr 9. PubMed PMID: 25864612. 13: BAER JE, BEYER KH, PAULSON SF, RUSSO HF. Renal elimination of 3-methylaminoisocamphane hydrochloride (mecamylamine). Am J Physiol. 1956 Jul;186(1):180-6. PubMed PMID: 13354778. 14: STONE CA, TORCHIANA ML, NAVARRO A, BEYER KH. Ganglionic blocking properties of 3-methylaminoisocamphane hydrochloride (mecamylamine): a secondary amine. J Pharmacol Exp Ther. 1956 Jun;117(2):169-83. PubMed PMID: 13332559. 15: ZAWOISKI EJ, BAER JE, BRAUNSCHWEIG LW, PAULSON SF, SHERMER A, BEYER KH. Gastrointestinal secretion and absorption of 3-methylaminoisocamphane hydrochloride (mecamylamine). J Pharmacol Exp Ther. 1958 Apr;122(4):442-8. PubMed PMID: 13539770. 16: WALDRON JF. Ileus due to mecamylamine hydrochloride; simulating an acute surgical condition of the abdomen. Minn Med. 1958 Jul;41(7):499-502. PubMed PMID: 13565864. 17: MENDEZ L, FIGUEROA G. [Experiments with a new ganglion-blocking agent, mecamylamine hydrochloride in the treatment of arterial hypertension]. Arch Inst Cardiol Mex. 1957 Jul-Aug;27(4):399-410. Spanish. PubMed PMID: 13471314. 18: Figallo EM, Wingard LB Jr. Effects of physostigmine, scopolamine, and mecamylamine on the sleeping time induced by ketamine in the rat. Psychopharmacology (Berl). 1979 Mar 14;61(1):59-62. PubMed PMID: 108720. 19: BARBANO G. [Clinical observations on a new hypotensive preparation with ganglioplegic action (mecamylamine hydrochloride)]. Minerva Med. 1957 Oct 24;48(85):3551-4. English, Italian. PubMed PMID: 13493211. 20: MARCHETTI G, NAVA S, TARTARA A. [Experimental & clinical observation on the activity of a new synthetic ganglioplegic: mecamylamine (3-methylaminoisocamphane hydrochloride)]. Minerva Med. 1958 Feb 21;49(15):606-14. Italian. PubMed PMID: 13541046.