Iodopravadoline | AM630 | CAS#164178-33-0 | cannabinoid CB1 receptor agonist

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

MedKoo CAT#: 319600

CAS#: 164178-33-0

Description: Iodopravadoline, also known as AM630, is an inverse agonist at the human cannabinoid CB1 receptor. Iodopravadoline has been found to attenuate the ability of a number of cannabinoids to inhibit electrically-evoked twitches of the mouse isolated vas deferens. AM630 was markedly more potent as an antagonist of delta 9-THC and CP 55,940 (Kd = 14.0 and 17.3 nM respectively) than as an antagonist of WIN 55,212-2, AM356 or anandamide (Kd = 36.5, 85.9 and 278.8 nM respectively).

Chemical Structure

Iodopravadoline

CAS# 164178-33-0

Product data Instruction

Theoretical Analysis

MedKoo Cat#: 319600
Name: Iodopravadoline
CAS#: 164178-33-0
Chemical Formula: C23H25IN2O3
Exact Mass: 504.09
Molecular Weight: 504.369
Elemental Analysis: C, 54.77; H, 5.00; I, 25.16; N, 5.55; O, 9.52

Price and Availability

Size	Price	Availability
5mg	USD 275	2 Weeks
10mg	USD 450	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.

Synonym: AM630; AM-630; AM 630; iodopravadoline.

IUPAC/Chemical Name: (6-iodo-2-methyl-1-(2-morpholinoethyl)-1H-indol-3-yl)(4-methoxyphenyl)methanone

InChi Key: JHOTYHDSLIUKCJ-UHFFFAOYSA-N

InChi Code: InChI=1S/C23H25IN2O3/c1-16-22(23(27)17-3-6-19(28-2)7-4-17)20-8-5-18(24)15-21(20)26(16)10-9-25-11-13-29-14-12-25/h3-8,15H,9-14H2,1-2H3

SMILES Code: O=C(C1=C(C)N(CCN2CCOCC2)C3=C1C=CC(I)=C3)C4=CC=C(OC)C=C4

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, 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:

Product Data:

Product Data

Instruction:

View handling instruction

Biological target:	Iodopravadoline, also known as AM630, is an inverse agonist at the human cannabinoid CB1 receptor.
In vitro activity:	The next objective was to probe for differences in the the GBM-derived cell lines by looking at the expression changes driven by the CB2 receptor inverse agonist AM630. This study found that AM630 drove a substantial transcriptional response in the core cell population. Reference: Molecules. 2022 Mar 22;27(7):2049. https://pubmed.ncbi.nlm.nih.gov/35408449/
In vivo activity:	WIN-induced inhibition of CAP responses in sensory neurons was reversed by AM630 pre-treatment and AM251 co-treatment (25 μM each), as these conditions inhibit WIN responses. Hindpaw injections of AM630 and AM251 did not produce nocifensive behaviors. However, both compounds modulated CAP-induced thermal hyperalgesia in wild-type mice and rats, but not TRPA1 null-mutant mice. Reference: Neuropharmacology. 2011 Sep;61(4):778-88. https://pubmed.ncbi.nlm.nih.gov/21645531/

Solubility Data

	Solvent	Max Conc. mg/mL	Max Conc. mM
Solubility
	DMSO	50.4	100.00

Preparing Stock Solutions

The following data is based on the product molecular weight 504.37 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. Williams G, Chambers D, Rahman R, Molina-Holgado F. Transcription Profile and Pathway Analysis of the Endocannabinoid Receptor Inverse Agonist AM630 in the Core and Infiltrative Boundary of Human Glioblastoma Cells. Molecules. 2022 Mar 22;27(7):2049. doi: 10.3390/molecules27072049. PMID: 35408449; PMCID: PMC9000751. 2. Li W, Sun Y. Nrf2 is required for suppressing osteoclast RANKL-induced differentiation in RAW 264.7 cells via inactivating cannabinoid receptor type 2 with AM630. Regen Ther. 2020 Mar 2;14:191-195. doi: 10.1016/j.reth.2020.02.001. PMID: 32154333; PMCID: PMC7056625. 3. Patil M, Patwardhan A, Salas MM, Hargreaves KM, Akopian AN. Cannabinoid receptor antagonists AM251 and AM630 activate TRPA1 in sensory neurons. Neuropharmacology. 2011 Sep;61(4):778-88. doi: 10.1016/j.neuropharm.2011.05.024. Epub 2011 May 27. PMID: 21645531; PMCID: PMC3130079.
In vitro protocol:	1. Williams G, Chambers D, Rahman R, Molina-Holgado F. Transcription Profile and Pathway Analysis of the Endocannabinoid Receptor Inverse Agonist AM630 in the Core and Infiltrative Boundary of Human Glioblastoma Cells. Molecules. 2022 Mar 22;27(7):2049. doi: 10.3390/molecules27072049. PMID: 35408449; PMCID: PMC9000751. 2. Li W, Sun Y. Nrf2 is required for suppressing osteoclast RANKL-induced differentiation in RAW 264.7 cells via inactivating cannabinoid receptor type 2 with AM630. Regen Ther. 2020 Mar 2;14:191-195. doi: 10.1016/j.reth.2020.02.001. PMID: 32154333; PMCID: PMC7056625.
In vivo protocol:	1. Patil M, Patwardhan A, Salas MM, Hargreaves KM, Akopian AN. Cannabinoid receptor antagonists AM251 and AM630 activate TRPA1 in sensory neurons. Neuropharmacology. 2011 Sep;61(4):778-88. doi: 10.1016/j.neuropharm.2011.05.024. Epub 2011 May 27. PMID: 21645531; PMCID: PMC3130079.

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1: Patil M, Patwardhan A, Salas MM, Hargreaves KM, Akopian AN. Cannabinoid receptor antagonists AM251 and AM630 activate TRPA1 in sensory neurons. Neuropharmacology. 2011 Sep;61(4):778-88. doi: 10.1016/j.neuropharm.2011.05.024. Epub 2011 May 27. PubMed PMID: 21645531; PubMed Central PMCID: PMC3130079.

2: Bolognini D, Cascio MG, Parolaro D, Pertwee RG. AM630 behaves as a protean ligand at the human cannabinoid CB2 receptor. Br J Pharmacol. 2012 Apr;165(8):2561-74. doi: 10.1111/j.1476-5381.2011.01503.x. PubMed PMID: 21615724; PubMed Central PMCID: PMC3423246.

3: Geng DC, Xu YZ, Yang HL, Zhu XS, Zhu GM, Wang XB. Inhibition of titanium particle-induced inflammatory osteolysis through inactivation of cannabinoid receptor 2 by AM630. J Biomed Mater Res A. 2010 Oct;95(1):321-6. doi: 10.1002/jbm.a.32836. PubMed PMID: 20623669.

4: Werner NA, Koch JE. Effects of the cannabinoid antagonists AM281 and AM630 on deprivation-induced intake in Lewis rats. Brain Res. 2003 Mar 28;967(1-2):290-2. PubMed PMID: 12650991.

5: Ross RA, Brockie HC, Stevenson LA, Murphy VL, Templeton F, Makriyannis A, Pertwee RG. Agonist-inverse agonist characterization at CB1 and CB2 cannabinoid receptors of L759633, L759656, and AM630. Br J Pharmacol. 1999 Feb;126(3):665-72. PubMed PMID: 10188977; PubMed Central PMCID: PMC1565857.

6: Landsman RS, Makriyannis A, Deng H, Consroe P, Roeske WR, Yamamura HI. AM630 is an inverse agonist at the human cannabinoid CB1 receptor. Life Sci. 1998;62(9):PL109-13. PubMed PMID: 9496703.

7: Hosohata Y, Quock RM, Hosohata K, Makriyannis A, Consroe P, Roeske WR, Yamamura HI. AM630 antagonism of cannabinoid-stimulated [35S]GTP gamma S binding in the mouse brain. Eur J Pharmacol. 1997 Feb 19;321(1):R1-3. PubMed PMID: 9083796.

8: Hosohata K, Quock RM, Hosohata Y, Burkey TH, Makriyannis A, Consroe P, Roeske WR, Yamamura HI. AM630 is a competitive cannabinoid receptor antagonist in the guinea pig brain. Life Sci. 1997;61(9):PL115-8. PubMed PMID: 9284087.

9: Pertwee R, Griffin G, Fernando S, Li X, Hill A, Makriyannis A. AM630, a competitive cannabinoid receptor antagonist. Life Sci. 1995;56(23-24):1949-55. PubMed PMID: 7776818.

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