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MedKoo Cat#: 319600 | Name: Iodopravadoline
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Description:

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

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
Iodopravadoline
CAS#164178-33-0

Theoretical Analysis

MedKoo Cat#: 319600

Name: Iodopravadoline

CAS#: 164178-33-0

Chemical Formula: C23H25IN2O3

Exact Mass: 504.0910

Molecular Weight: 504.37

Elemental Analysis: C, 54.77; H, 5.00; I, 25.16; N, 5.55; O, 9.52

Price and Availability

Size Price Availability Quantity
5mg USD 350.00 2 Weeks
10mg USD 550.00 2 Weeks
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Related CAS #
No Data
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/
Solvent mg/mL mM
Solubility
DMSO 50.4 100.00
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 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.

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. 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.
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.