Clorgyline HCl | 17780-75-5 (HCl) | MAOI

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

MedKoo CAT#: 329655

CAS#: 17780-75-5 (HCl)

Description: Clorgyline, also known as Clorgiline, M&B 9302 or MB9302, is a monoamine oxidase inhibitor (MAOI) structurally related to pargyline which is described as an antidepressant. Specifically, it is an irreversible and selective inhibitor of monoamine oxidase A (MAO-A). Clorgiline was never marketed, but it has found use in scientific research. In addition to its actions as an MAOI, clorgiline has been found to bind with high affinity to the σ1 receptor (Ki = 3.2 nM) and with very high affinity to the I2 imidazoline receptor (an allosteric site on the monoamine oxidase enzyme) (Ki = 40 pM).

Chemical Structure

Clorgyline HCl

CAS# 17780-75-5 (HCl)

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 329655
Name: Clorgyline HCl
CAS#: 17780-75-5 (HCl)
Chemical Formula: C13H16Cl3NO
Exact Mass: 0.00
Molecular Weight: 308.627
Elemental Analysis: C, 50.59; H, 5.23; Cl, 34.46; N, 4.54; O, 5.18

Price and Availability

Size	Price	Availability
100mg	USD 350	2 Weeks
200mg	USD 600	2 Weeks
500mg	USD 1050	2 Weeks
1g	USD 1950	2 Weeks
2g	USD 3450	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 #: 17780-72-2 (free base) 17780-75-5 (HCl)

Synonym: Clorgyline HCl; Clorgyline hydrochloride; M&B 9302; MB 9302; MB-9302; MB9302; Clorgiline

IUPAC/Chemical Name: N-(3-(2,4-dichlorophenoxy)propyl)-N-methylprop-2-yn-1-amine hydrochloride

InChi Key: BBAZDLONIUABKI-UHFFFAOYSA-N

InChi Code: InChI=1S/C13H15Cl2NO.ClH/c1-3-7-16(2)8-4-9-17-13-6-5-11(14)10-12(13)15;/h1,5-6,10H,4,7-9H2,2H3;1H

SMILES Code: C#CCN(CCCOC1=CC=C(Cl)C=C1Cl)C.[H]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: >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:

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Biological target:	Clorgyline hydrochloride is an irreversible and selective inhibitor of monoamine oxidase A (MAO-A) that is used in scientific research; structurally related to Pargyline.
In vitro activity:	Clorgyline inhibited CaCdr1p efflux activity by 98.2% and also inhibited CaCdr2p by 93.8%. Reference: Antimicrob Agents Chemother. 2012 Mar; 56(3): 1508–1515. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3294898/
In vivo activity:	This study first assessed the effect of different doses of clorgyline treatment (0.5, 1.5, or 3 mg/kg) on the enzymatic activity of MAO-A in the cortex of WT mice. Clorgyline treatment for 21 days resulted in a significant inhibition of MAO-A enzymatic activity compared with vehicle-treated animals (Fig. 2A; one-way ANOVA with Tukey's post hoc analysis; p < 0.0001). Reference: Exp Neurol. 2016 Apr;278:4-10. https://pubmed.ncbi.nlm.nih.gov/26825854/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	55.0	178.21
	DMF	15.0	48.60
	Ethanol	15.0	48.60
	Ethanol:PBS (pH 7.2) (1:10)	0.3	0.81
	Water	120.0	388.82

Preparing Stock Solutions

The following data is based on the product molecular weight 308.63 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:	1. Holmes AR, Keniya MV, Ivnitski-Steele I, Monk BC, Lamping E, Sklar LA, Cannon RD. The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates. Antimicrob Agents Chemother. 2012 Mar;56(3):1508-15. doi: 10.1128/AAC.05706-11. Epub 2011 Dec 27. PMID: 22203607; PMCID: PMC3294898. 2. Garcia-Miralles M, Ooi J, Ferrari Bardile C, Tan LJ, George M, Drum CL, Lin RY, Hayden MR, Pouladi MA. Treatment with the MAO-A inhibitor clorgyline elevates monoamine neurotransmitter levels and improves affective phenotypes in a mouse model of Huntington disease. Exp Neurol. 2016 Apr;278:4-10. doi: 10.1016/j.expneurol.2016.01.019. Epub 2016 Jan 26. PMID: 26825854. 3. Ledesma JC, Escrig MA, Pastor R, Aragon CM. The MAO-A inhibitor clorgyline reduces ethanol-induced locomotion and its volitional intake in mice. Pharmacol Biochem Behav. 2014 Jan;116:30-8. doi: 10.1016/j.pbb.2013.11.012. Epub 2013 Nov 16. PMID: 24252443.
In vitro protocol:	1. Holmes AR, Keniya MV, Ivnitski-Steele I, Monk BC, Lamping E, Sklar LA, Cannon RD. The monoamine oxidase A inhibitor clorgyline is a broad-spectrum inhibitor of fungal ABC and MFS transporter efflux pump activities which reverses the azole resistance of Candida albicans and Candida glabrata clinical isolates. Antimicrob Agents Chemother. 2012 Mar;56(3):1508-15. doi: 10.1128/AAC.05706-11. Epub 2011 Dec 27. PMID: 22203607; PMCID: PMC3294898.
In vivo protocol:	1. Garcia-Miralles M, Ooi J, Ferrari Bardile C, Tan LJ, George M, Drum CL, Lin RY, Hayden MR, Pouladi MA. Treatment with the MAO-A inhibitor clorgyline elevates monoamine neurotransmitter levels and improves affective phenotypes in a mouse model of Huntington disease. Exp Neurol. 2016 Apr;278:4-10. doi: 10.1016/j.expneurol.2016.01.019. Epub 2016 Jan 26. PMID: 26825854. 2. Ledesma JC, Escrig MA, Pastor R, Aragon CM. The MAO-A inhibitor clorgyline reduces ethanol-induced locomotion and its volitional intake in mice. Pharmacol Biochem Behav. 2014 Jan;116:30-8. doi: 10.1016/j.pbb.2013.11.012. Epub 2013 Nov 16. PMID: 24252443.

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1: Fowler CJ, Oreland L, Callingham BA. The acetylenic monoamine oxidase inhibitors clorgyline, deprenyl, pargyline and J-508: their properties and applications. J Pharm Pharmacol. 1981 Jun;33(6):341-7. doi: 10.1111/j.2042-7158.1981.tb13800.x. PMID: 6115003.

2: Fowler JS, Ding YS, Logan J, MacGregor RR, Shea C, Garza V, Gimi R, Volkow ND, Wang GJ, Schlyer D, Ferrieri R, Gatley SJ, Alexoff D, Carter P, King P, Pappas N, Arnett CD. Species differences in [11C]clorgyline binding in brain. Nucl Med Biol. 2001 Oct;28(7):779-85. doi: 10.1016/s0969-8051(01)00245-1. PMID: 11578898.

3: Fowler JS, Logan J, Ding YS, Franceschi D, Wang GJ, Volkow ND, Pappas N, Schlyer D, Gatley SJ, Alexoff D, Felder C, Biegon A, Zhu W. Non-MAO A binding of clorgyline in white matter in human brain. J Neurochem. 2001 Dec;79(5):1039-46. doi: 10.1046/j.1471-4159.2001.00649.x. PMID: 11739617.

4: Culver KE, Szechtman H. Clorgyline-induced switch from locomotion to mouthing in sensitization to the dopamine D2/D3 agonist quinpirole in rats: role of sigma and imidazoline I2 receptors. Psychopharmacology (Berl). 2003 May;167(2):211-8. doi: 10.1007/s00213-003-1408-z. Epub 2003 Mar 22. PMID: 12652347.

5: Kitanaka N, Kitanaka J, Watabe K, Takemura M. Low-dose pretreatment with clorgyline decreases the levels of 3-methoxy-4-hydroxyphenylglycol in the striatum and nucleus accumbens and attenuates methamphetamine-induced conditioned place preference in rats. Neuroscience. 2010 Feb 17;165(4):1370-6. doi: 10.1016/j.neuroscience.2009.11.058. Epub 2009 Dec 1. PMID: 19958817.

6: Katayama S, Shigemi K, Cline MA, Furuse M. Clorgyline inhibits orexin-A- induced arousal in layer-type chicks. J Vet Med Sci. 2011 Apr;73(4):471-4. doi: 10.1292/jvms.10-0358. Epub 2010 Nov 10. PMID: 21079379.

7: Potter WZ, Murphy DL, Wehr TA, Linnoila M, Goodwin FK. Clorgyline. A new treatment for patients with refractory rapid-cycling disorder. Arch Gen Psychiatry. 1982 May;39(5):505-10. doi: 10.1001/archpsyc.1982.04290050001001. PMID: 6807254.

8: Ledesma JC, Escrig MA, Pastor R, Aragon CM. The MAO-A inhibitor clorgyline reduces ethanol-induced locomotion and its volitional intake in mice. Pharmacol Biochem Behav. 2014 Jan;116:30-8. doi: 10.1016/j.pbb.2013.11.012. Epub 2013 Nov 16. PMID: 24252443.

9: O'Brien EM, Tipton KF, Meroni M, Dostert P. Inhibition of monoamine oxidase by clorgyline analogues. J Neural Transm Suppl. 1994;41:295-305. doi: 10.1007/978-3-7091-9324-2_39. PMID: 7931241.

10: Xie SS, Liu J, Tang C, Pang C, Li Q, Qin Y, Nong X, Zhang Z, Guo J, Cheng M, Tang W, Liang N, Jiang N. Design, synthesis and biological evaluation of rasagiline-clorgyline hybrids as novel dual inhibitors of monoamine oxidase-B and amyloid-β aggregation against Alzheimer's disease. Eur J Med Chem. 2020 Sep 15;202:112475. doi: 10.1016/j.ejmech.2020.112475. Epub 2020 Jun 30. PMID: 32652406.

11: Ari G, Finberg JP. Effects of clorgyline on the release of noradrenaline from rat vas deferens. Eur J Pharmacol. 1992 Aug 14;219(1):89-96. doi: 10.1016/0014-2999(92)90584-q. PMID: 1397052.

12: Murphy DL, Lipper S, Slater S, Shiling D. Selectivity of clorgyline and pargyline as inhibitors of monoamine oxidases A and B in vivo in man. Psychopharmacology (Berl). 1979 Apr 11;62(2):129-32. doi: 10.1007/BF00427125. PMID: 111275.

13: Tamarkin L, Craig CJ, Garrick NA, Wehr TA. Effect of clorgyline (a MAO type A inhibitor) on locomotor activity in the Syrian hamster. Am J Physiol. 1983 Aug;245(2):R215-21. doi: 10.1152/ajpregu.1983.245.2.R215. PMID: 6881380.

14: Ross RJ, Scheinin M, Lesieur P, Rudorfer MV, Hauger RL, Siever LJ, Linnoila M, Potter WZ. The effect of clorgyline on noradrenergic function. Psychopharmacology (Berl). 1985;85(2):227-30. doi: 10.1007/BF00428420. PMID: 3925487.

15: Kitanaka N, Kitanaka J, Takemura M. Modification of morphine-induced hyperlocomotion and antinociception in mice by clorgyline, a monoamine oxidase-A inhibitor. Neurochem Res. 2006 Jun;31(6):829-37. doi: 10.1007/s11064-006-9087-x. Epub 2006 Jun 23. PMID: 16794857.

16: Mihalik J, Mašlanková J, Špakovská T, Mareková M, Hodorová I, Kušnír J, Rybárová S, Ferenc P, Schmidtová K. Impact of 2 doses of clorgyline on the rat preimplantation embryo development and the monoamine levels in urine. Reprod Sci. 2010 Aug;17(8):734-41. doi: 10.1177/1933719110369181. PMID: 20595704.

17: Mateo Y, Fernández-Pastor B, Meana JJ. Acute and chronic effects of desipramine and clorgyline on alpha(2)-adrenoceptors regulating noradrenergic transmission in the rat brain: a dual-probe microdialysis study. Br J Pharmacol. 2001 Aug;133(8):1362-70. doi: 10.1038/sj.bjp.0704196. PMID: 11498523; PMCID: PMC1621148.

18: Kitanaka N, Kitanaka J, Takemura M. Repeated clorgyline treatment inhibits methamphetamine-induced behavioral sensitization in mice. Neurochem Res. 2005 Apr;30(4):445-51. doi: 10.1007/s11064-005-2679-z. PMID: 16076014.

19: Suzuki T, Akaike N, Ueno K, Tanaka Y, Himori N. MAO inhibitors, clorgyline and lazabemide, prevent hydroxyl radical generation caused by brain ischemia/reperfusion in mice. Pharmacology. 1995 Jun;50(6):357-62. doi: 10.1159/000139304. PMID: 7568334.

20: Sitges M, Aldana BI, Chiu LM, Nekrassov V. Characterization of phenytoin, carbamazepine, vinpocetine and clorgyline simultaneous effects on sodium channels and catecholamine metabolism in rat striatal nerve endings. Neurochem Res. 2009 Mar;34(3):470-9. doi: 10.1007/s11064-008-9805-7. Epub 2008 Aug 19. PMID: 18712476.

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