Caramiphen hydrochloride | CAS# 125-85-9 (HCl) | antimuscarinic and anticholinergic

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

MedKoo CAT#: 412289

CAS#: 125-85-9 (HCl)

Description: Caramiphen hydrochloride is the salt form of Caramiphne (free base), which is an antimuscarinic and anticholinergic agent. It acts as an antagonist of NMDA receptor.

Chemical Structure

Caramiphen hydrochloride

CAS# 125-85-9 (HCl)

Instruction

Theoretical Analysis

MedKoo Cat#: 412289
Name: Caramiphen hydrochloride
CAS#: 125-85-9 (HCl)
Chemical Formula: C18H28ClNO2
Exact Mass: 325.18
Molecular Weight: 325.880
Elemental Analysis: C, 66.34; H, 8.66; Cl, 10.88; N, 4.30; O, 9.82

Price and Availability

Size	Price	Availability
10mg	USD 485	2 Weeks
50mg	USD 1350	2 Weeks
Bulk inquiry Welcome, Customer: Please do not inquire quote if your intended use is for a patient since our products are for research use and for chemical synthesis use, not for human use . For in-stock products, we listed price in the web page. You may inquire prices for which sizes were not listed. If no price is listed, this means the product is not in stock at the moment, which may be available via custom synthesis. For cost-effective reason, minimum order of 1g is requested (typically very expensive). The lead time is usually 2-4 months. Quote of less than 1g will not be provided. MedKoo may not offer quote for below reasons: (1) current available synthetic method appears to be extremely expensive which is obviously not affordable to most customers; (2) Key raw material to make the product is temporally not available; (3) DEA controlled substances; (4) the product is under patent protection in customer’s country.

Related CAS #: 77-22-5 (free base) 125-85-9 (HCl)

Synonym: Caramiphen hydrochloride; G2747; G-2747; G 2747

IUPAC/Chemical Name: 2-(diethylamino)ethyl 1-phenylcyclopentane-1-carboxylate hydrochloride

InChi Key: MUPNXGNOIBYHSG-UHFFFAOYSA-N

InChi Code: InChI=1S/C18H27NO2.ClH/c1-3-19(4-2)14-15-21-17(20)18(12-8-9-13-18)16-10-6-5-7-11-16;/h5-7,10-11H,3-4,8-9,12-15H2,1-2H3;1H

SMILES Code: CCN(CCOC(C1(c2ccccc2)CCCC1)=O)CC.Cl

Appearance: 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

Shelf Life: >3 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:

Instruction:

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Biological target:
In vitro activity:
In vivo activity:

Preparing Stock Solutions

The following data is based on the product molecular weight 325.88 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

Formulation protocol:
In vitro protocol:
In vivo protocol:

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1: Raveh L, Eisenkraft A, Weissman BA. Caramiphen edisylate: an optimal antidote against organophosphate poisoning. Toxicology. 2014 Nov 5;325:115-24. doi: 10.1016/j.tox.2014.09.005. Epub 2014 Sep 6. PMID: 25201353.

2: Leung YM, Tzeng JI, Gong CL, Wang YW, Chen YW, Wang JJ. Caramiphen-induced block of sodium currents and spinal anesthesia. Eur J Pharmacol. 2015 Jan 5;746:213-20. doi: 10.1016/j.ejphar.2014.10.035. Epub 2014 Oct 29. PMID: 25446426.

3: Figueiredo TH, Aroniadou-Anderjaska V, Qashu F, Apland JP, Pidoplichko V, Stevens D, Ferrara TM, Braga MF. Neuroprotective efficacy of caramiphen against soman and mechanisms of its action. Br J Pharmacol. 2011 Nov;164(5):1495-505. doi: 10.1111/j.1476-5381.2011.01427.x. PMID: 21486285; PMCID: PMC3221103.

4: Schultz MK, Wright LK, de Araujo Furtado M, Stone MF, Moffett MC, Kelley NR, Bourne AR, Lumeh WZ, Schultz CR, Schwartz JE, Lumley LA. Caramiphen edisylate as adjunct to standard therapy attenuates soman-induced seizures and cognitive deficits in rats. Neurotoxicol Teratol. 2014 Jul-Aug;44:89-104. doi: 10.1016/j.ntt.2014.06.002. Epub 2014 Jun 16. PMID: 24946037.

5: Raveh L, Weissman BA, Cohen G, Alkalay D, Rabinovitz I, Sonego H, Brandeis R. Caramiphen and scopolamine prevent soman-induced brain damage and cognitive dysfunction. Neurotoxicology. 2002 May;23(1):7-17. doi: 10.1016/s0161-813x(02)00005-0. PMID: 12164550.

6: Hung CH, Chu CC, Chen YC, Liu KS, Chen YW, Wang JJ. Cutaneous analgesia and systemic toxicity of carbetapentane and caramiphen in rats. Reg Anesth Pain Med. 2012 Jan-Feb;37(1):34-9. doi: 10.1097/AAP.0b013e318237f6ab. PMID: 22157742.

7: De Araujo Furtado M, Aroniadou-Anderjaska V, Figueiredo TH, Apland JP, Braga MFM. Electroencephalographic analysis in soman-exposed 21-day-old rats and the effects of midazolam or LY293558 with caramiphen. Ann N Y Acad Sci. 2020 Nov;1479(1):122-133. doi: 10.1111/nyas.14331. Epub 2020 Mar 31. PMID: 32237259.

8: CARAMIPHEN hydrochloride. J Am Med Assoc. 1959 Apr 25;169(17):2019. PMID: 13640966.

9: Hudkins RL, Stubbins JF, DeHaven-Hudkins DL. Caramiphen, iodocaramiphen and nitrocaramiphen are potent, competitive, muscarinic M1 receptor-selective agents. Eur J Pharmacol. 1993 Feb 16;231(3):485-8. doi: 10.1016/0014-2999(93)90130-a. PMID: 8449241.

10: Chen YW, Chu CC, Chen YC, Wang JJ, Hung CH. Isobolographic analysis of caramiphen and lidocaine on spinal anesthesia in rats. Neurosci Lett. 2010 Jan 18;469(1):174-8. doi: 10.1016/j.neulet.2009.11.071. Epub 2009 Dec 3. PMID: 19962431.

11: DeHaven-Hudkins DL, Allen JT, Hudkins RL, Stubbins JF, Tortella FC. Anticonvulsant activity of caramiphen analogs. Life Sci. 1995;56(19):1571-6. doi: 10.1016/0024-3205(95)00123-n. PMID: 7723585.

12: Tortella FC, Witkin JM, Musacchio JM. Caramiphen: a non-opioid antitussive with potent anticonvulsant properties in rats. Eur J Pharmacol. 1988 Oct 11;155(1-2):69-75. doi: 10.1016/0014-2999(88)90403-7. PMID: 3243332.

13: Figueiredo TH, Aroniadou-Anderjaska V, Apland JP, Rossetti K, Braga MF. Delayed tezampanel and caramiphen treatment but not midazolam protects against long-term neuropathology after soman exposure. Exp Biol Med (Maywood). 2023 Apr;248(7):612-623. doi: 10.1177/15353702231171911. Epub 2023 Jun 10. PMID: 37300407; PMCID: PMC10350803.

14: Kawaura K, Miki R, Shima E, Honda S, Soeda F, Shirasaki T, Takahama K. Antidepressant-like effect of centrally acting non-narcotic antitussive caramiphen in a forced swimming test. Neurosci Lett. 2010 Sep 13;481(3):188-90. doi: 10.1016/j.neulet.2010.07.003. Epub 2010 Jul 16. PMID: 20621160.

15: Székely JI, Sharpe LG, Katz JL. Effects of caramiphen and phencyclidine alone and in combination on behavior in the rat. Pharmacol Biochem Behav. 1994 Mar;47(3):709-13. doi: 10.1016/0091-3057(94)90177-5. PMID: 8208792.

16: Domino EF, Krutak-Krol H, Lal J. Evidence for a central site of action for the antitussive effects of caramiphen. J Pharmacol Exp Ther. 1985 Apr;233(1):249-53. PMID: 3981459.

17: Raveh L, Rabinovitz I, Gilat E, Egoz I, Kapon J, Stavitsky Z, Weissman BA, Brandeis R. Efficacy of antidotal treatment against sarin poisoning: the superiority of benactyzine and caramiphen. Toxicol Appl Pharmacol. 2008 Feb 15;227(1):155-62. doi: 10.1016/j.taap.2007.10.020. PMID: 18320638.

18: Schultz MK, Wright LK, Stone MF, Schwartz JE, Kelley NR, Moffett MC, Lee RB, Lumley LA. The anticholinergic and antiglutamatergic drug caramiphen reduces seizure duration in soman-exposed rats: synergism with the benzodiazepine diazepam. Toxicol Appl Pharmacol. 2012 Mar 15;259(3):376-86. doi: 10.1016/j.taap.2012.01.017. Epub 2012 Jan 30. PMID: 22310180.

19: Apland JP, Aroniadou-Anderjaska V, Figueiredo TH, Pidoplichko VI, Rossetti K, Braga MFM. Comparing the Antiseizure and Neuroprotective Efficacy of LY293558, Diazepam, Caramiphen, and LY293558-Caramiphen Combination against Soman in a Rat Model Relevant to the Pediatric Population. J Pharmacol Exp Ther. 2018 May;365(2):314-326. doi: 10.1124/jpet.117.245969. Epub 2018 Feb 21. PMID: 29467308; PMCID: PMC5878669.

20: Apland JP, Aroniadou-Anderjaska V, Figueiredo TH, De Araujo Furtado M, Braga MFM. Full Protection Against Soman-Induced Seizures and Brain Damage by LY293558 and Caramiphen Combination Treatment in Adult Rats. Neurotox Res. 2018 Oct;34(3):511-524. doi: 10.1007/s12640-018-9907-1. Epub 2018 Apr 30. PMID: 29713995.

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