Dexmecamylamine HCl | TC-5214 | NIH-11008 | CAS#107596-30-5 | 107538-05-6 | nicotinic channel modulator

MedKoo Cat#: 319729 | Name: Dexmecamylamine HCl

Description:

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

Dexmecamylamine, also known as TC-5214 and NIH-11008, is a nicotinic channel modulator with antidepressant activity. TC-5214 demonstrated positive effects in a number of animal models of depression and anxiety. TC-5214 was active in the forced swim test in rats (minimum effective dose (MED)=3 mg/kg i.p.), a classical depression model. It was also active in the behavioral despair test in mice (0.1-3.0 mg/kg i.p.), another model of depression.

Chemical Structure

Dexmecamylamine HCl

CAS#107596-30-5 (HCl)

Theoretical Analysis

MedKoo Cat#: 319729

Name: Dexmecamylamine HCl

CAS#: 107596-30-5 (HCl)

Chemical Formula: C11H22ClN

Exact Mass: 167.1674

Molecular Weight: 203.75

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

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.

Bulk Inquiry

Related CAS #

107538-05-6 (free base) 107596-30-5 (HCl)

Synonym

TC-5214; TC 5214; TC5214; NIH-11008; NIH 11008; NIH11008; Dexmecamylamine; Dexmecamylamine HCl

IUPAC/Chemical Name

(1R,2S,4S)-N,2,3,3-tetramethylbicyclo[2.2.1]heptan-2-amine hydrochloride

InChi Key

PKVZBNCYEICAQP-GSTSRXQZSA-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/t8-,9+,11-;/m0./s1

SMILES Code

CC1(C)[C@](NC)(C)[C@]2([H])CC[C@@]1([H])C2.[H]Cl

Appearance

White to off-white solid powder

Purity

>98% (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, not in water

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

Related CAS# 107538-05-6 (Dexmecamylamine) 107596-30-5 (Dexmecamylamine hydrochloride)

Instruction

View handling instruction

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.

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

1: Zhao HP, Xiang BR. Discontinued cardiovascular drugs in 2013 and 2014. Expert Opin Investig Drugs. 2015;24(8):1083-92. doi: 10.1517/13543784.2015.1051619. PubMed PMID: 26162717. 2: Möller HJ, Demyttenaere K, Olausson B, Szamosi J, Wilson E, Hosford D, Dunbar G, Tummala R, Eriksson H. Two Phase III randomised double-blind studies of fixed-dose TC-5214 (dexmecamylamine) adjunct to ongoing antidepressant therapy in patients with major depressive disorder and an inadequate response to prior antidepressant therapy. World J Biol Psychiatry. 2015 Oct;16(7):483-501. doi: 10.3109/15622975.2014.989261. Epub 2015 Jan 20. PubMed PMID: 25602163. 3: Tummala R, Desai D, Szamosi J, Wilson E, Hosford D, Dunbar G, Eriksson H. Safety and tolerability of dexmecamylamine (TC-5214) adjunct to ongoing antidepressant therapy in patients with major depressive disorder and an inadequate response to antidepressant therapy: results of a long-term study. J Clin Psychopharmacol. 2015 Feb;35(1):77-81. doi: 10.1097/JCP.0000000000000269. PubMed PMID: 25514064. 4: Alverlind S, Barassin S, Dalén P, Li Y, Toler S, Eriksson H, Tummala R. Clinical pharmacokinetics of the nicotinic channel modulator dexmecamylamine (TC-5214) in subjects with various degrees of renal impairment. Clin Drug Investig. 2014 Jul;34(7):457-65. doi: 10.1007/s40261-014-0195-0. PubMed PMID: 24760402. 5: Vieta E, Thase ME, Naber D, D'Souza B, Rancans E, Lepola U, Olausson B, Szamosi J, Wilson E, Hosford D, Dunbar G, Tummala R, Eriksson H. Efficacy and tolerability of flexibly-dosed adjunct TC-5214 (dexmecamylamine) in patients with major depressive disorder and inadequate response to prior antidepressant. Eur Neuropsychopharmacol. 2014 Apr;24(4):564-74. doi: 10.1016/j.euroneuro.2013.12.008. Epub 2013 Dec 21. PubMed PMID: 24507016. 6: Xu H, Henningsson A, Alverlind S, Tummala R, Toler S, Beaver JS, Al-Huniti N. Population pharmacokinetics of TC-5214, a nicotinic channel modulator, in phase I and II clinical studies. J Clin Pharmacol. 2014 Jun;54(6):707-18. doi: 10.1002/jcph.264. Epub 2014 Jan 16. PubMed PMID: 24408516. 7: Papke RL, Stokes C, Muldoon P, Imad Damaj M. Similar activity of mecamylamine stereoisomers in vitro and in vivo. Eur J Pharmacol. 2013 Nov 15;720(1-3):264-75. doi: 10.1016/j.ejphar.2013.10.018. Epub 2013 Oct 23. PubMed PMID: 24161916; PubMed Central PMCID: PMC3992716. 8: Lindsley CW. (S)-(+)-mecamylamine (TC-5214): a neuronal nicotinic receptor modulator enters phase III trials as an adjunct treatment for Major Depressive Disorder (MDD). ACS Chem Neurosci. 2010 Aug 18;1(8):530-1. doi: 10.1021/cn100070s. PubMed PMID: 22778844; PubMed Central PMCID: PMC3368682. 9: Lippiello PM, Beaver JS, Gatto GJ, James JW, Jordan KG, Traina VM, Xie J, Bencherif M. TC-5214 (S-(+)-mecamylamine): a neuronal nicotinic receptor modulator with antidepressant activity. CNS Neurosci Ther. 2008 Winter;14(4):266-77. doi: 10.1111/j.1755-5949.2008.00054.x. Review. PubMed PMID: 19040552. 10: Fedorov NB, Benson LC, Graef J, Lippiello PM, Bencherif M. Differential pharmacologies of mecamylamine enantiomers: positive allosteric modulation and noncompetitive inhibition. J Pharmacol Exp Ther. 2009 Feb;328(2):525-32. doi: 10.1124/jpet.108.146910. Epub 2008 Oct 28. PubMed PMID: 18957576.