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MedKoo Cat#: 130403 | Name: ACEA

Description:

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

ACEA is an agonist of the cannabinoid CB1 receptor and has been shown to alleviate brain ischemia/reperfusion injury through the CB1-Drp1 pathway.

Chemical Structure

ACEA
ACEA
CAS#220556-69-4

Theoretical Analysis

MedKoo Cat#: 130403

Name: ACEA

CAS#: 220556-69-4

Chemical Formula: C22H36ClNO

Exact Mass: 365.2485

Molecular Weight: 365.99

Elemental Analysis: C, 72.20; H, 9.92; Cl, 9.69; N, 3.83; O, 4.37

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.
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Related CAS #
No Data
Synonym
ACEA; Arachidonyl-2'-chloroethylamide
IUPAC/Chemical Name
(5Z,8Z,11Z,14Z)-N-(2-chloroethyl)icosa-5,8,11,14-tetraenamide
InChi Key
SCJNCDSAIRBRIA-DOFZRALJSA-N
InChi Code
InChI=1S/C22H36ClNO/c1-2-3-4-5-6-7-8-9-10-11-12-13-14-15-16-17-18-19-22(25)24-21-20-23/h6-7,9-10,12-13,15-16H,2-5,8,11,14,17-21H2,1H3,(H,24,25)/b7-6-,10-9-,13-12-,16-15-
SMILES Code
CCCCC/C=C\C/C=C\C/C=C\C/C=C\CCCC(NCCCl)=O
Appearance
To be determined
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
To be determined
Shelf Life
>2 years if stored properly
Drug Formulation
To be determined
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

Preparing Stock Solutions

The following data is based on the product molecular weight 365.99 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
1: Yang S, Hu B, Wang Z, Zhang C, Jiao H, Mao Z, Wei L, Jia J, Zhao J. Cannabinoid CB1 receptor agonist ACEA alleviates brain ischemia/reperfusion injury via CB1-Drp1 pathway. Cell Death Discov. 2020 Oct 12;6:102. doi: 10.1038/s41420-020-00338-3. PMID: 33083022; PMCID: PMC7548964. 2: Aso E, Palomer E, Juvés S, Maldonado R, Muñoz FJ, Ferrer I. CB1 agonist ACEA protects neurons and reduces the cognitive impairment of AβPP/PS1 mice. J Alzheimers Dis. 2012;30(2):439-59. doi: 10.3233/JAD-2012-111862. Erratum in: J Alzheimers Dis. 2012;31(3):679-80. PMID: 22451318. 3: Ma L, Jia J, Niu W, Jiang T, Zhai Q, Yang L, Bai F, Wang Q, Xiong L. Mitochondrial CB1 receptor is involved in ACEA-induced protective effects on neurons and mitochondrial functions. Sci Rep. 2015 Jul 28;5:12440. doi: 10.1038/srep12440. PMID: 26215450; PMCID: PMC4516969. 4: Andres-Mach M, Zolkowska D, Barcicka-Klosowska B, Haratym-Maj A, Florek- Luszczki M, Luszczki JJ. Effect of ACEA--a selective cannabinoid CB1 receptor agonist on the protective action of different antiepileptic drugs in the mouse pentylenetetrazole-induced seizure model. Prog Neuropsychopharmacol Biol Psychiatry. 2012 Dec 3;39(2):301-9. doi: 10.1016/j.pnpbp.2012.07.001. Epub 2012 Jul 10. PMID: 22789660. 5: Andres-Mach M, Haratym-Maj A, Zagaja M, Rola R, Maj M, Chrościńska-Krawczyk M, Luszczki JJ. ACEA (a highly selective cannabinoid CB1 receptor agonist) stimulates hippocampal neurogenesis in mice treated with antiepileptic drugs. Brain Res. 2015 Oct 22;1624:86-94. doi: 10.1016/j.brainres.2015.07.028. Epub 2015 Jul 29. PMID: 26225920. 6: Kozan R, Ayyildiz M, Agar E. The effects of intracerebroventricular AM-251, a CB1-receptor antagonist, and ACEA, a CB1-receptor agonist, on penicillin-induced epileptiform activity in rats. Epilepsia. 2009 Jul;50(7):1760-7. doi: 10.1111/j.1528-1167.2009.02098.x. Epub 2009 Apr 27. PMID: 19453709. 7: Zagaja M, Haratym-Maj A, Szewczyk A, Rola R, Maj M, Łuszczki JJ, Andres-Mach M. Levetiracetam combined with ACEA, highly selective cannabinoid CB1 receptor agonist changes neurogenesis in mouse brain. Neurosci Lett. 2019 Mar 23;696:79-86. doi: 10.1016/j.neulet.2018.12.016. Epub 2018 Dec 12. PMID: 30552944. 8: Asaadi S, Jahanbakhshi M, Lotfinia M, Naderi N. The Role of BK Channels in Antiseizure Action of the CB1 Receptor Agonist ACEA in Maximal Electroshock and Pentylenetetrazole Models of Seizure in Mice. Iran J Pharm Res. 2017 Spring;16(2):640-647. PMID: 28979317; PMCID: PMC5603872. 9: Rutkowska M, Fereniec-Gołebiewska L. Involvement of nitric oxide in the gastroprotective effect of ACEA, a selective cannabinoid CB1 receptor agonist, on aspirin-induced gastric ulceration. Pharmazie. 2009 Sep;64(9):595-7. PMID: 19827302. 10: Rutkowska M, Gliniak H. The influence of ACEA--a selective cannabinoid CB1 receptor agonist on whole blood and platelet-poor plasma serotonin concentrations. Pharmazie. 2009 Sep;64(9):598-601. PMID: 19827303. 11: Rutkowska M, Jachimczuk O. Antidepressant--like properties of ACEA (arachidonyl-2-chloroethylamide), the selective agonist of CB1 receptors. Acta Pol Pharm. 2004 Mar-Apr;61(2):165-7. PMID: 15493300. 12: Haddad M. The Impact of CB1 Receptor on Nuclear Receptors in Skeletal Muscle Cells. Pathophysiology. 2021 Oct 5;28(4):457-470. doi: 10.3390/pathophysiology28040029. PMID: 35366244; PMCID: PMC8830471. 13: Haddad M. The Impact of CB1 Receptor on Inflammation in Skeletal Muscle Cells. J Inflamm Res. 2021 Aug 14;14:3959-3967. doi: 10.2147/JIR.S322247. PMID: 34421307; PMCID: PMC8373309. 14: Rutkowska M, Fereniec-Gołtbiewska L. ACEA (arachidonyl-2-chloroethylamide), the selective cannabinoid CB1 receptor agonist, protects against aspirin-induced gastric ulceration. Pharmazie. 2006 Apr;61(4):341-2. PMID: 16649551. 15: Schuster J, Ates M, Brune K, Gühring H. The cannabinoids R(-)-7-hydroxy- delta-6-tetra-hydrocannabinol-dimethylheptyl (HU-210), 2-O-arachidonoylglycerylether (HU-310) and arachidonyl-2-chloroethylamide (ACEA) increase isoflurane provoked sleep duration by activation of cannabinoids 1 (CB1)-receptors in mice. Neurosci Lett. 2002 Jul 5;326(3):196-200. doi: 10.1016/s0304-3940(02)00302-6. PMID: 12095655. 16: Rodriguez-Arias M, Navarrete F, Daza-Losada M, Navarro D, Aguilar MA, Berbel P, Miñarro J, Manzanares J. CB1 cannabinoid receptor-mediated aggressive behavior. Neuropharmacology. 2013 Dec;75:172-80. doi: 10.1016/j.neuropharm.2013.07.013. Epub 2013 Aug 2. PMID: 23916480. 17: Marquart S, Zerr P, Akhmetshina A, Palumbo K, Reich N, Tomcik M, Horn A, Dees C, Engel M, Zwerina J, Distler O, Schett G, Distler JH. Inactivation of the cannabinoid receptor CB1 prevents leukocyte infiltration and experimental fibrosis. Arthritis Rheum. 2010 Nov;62(11):3467-76. doi: 10.1002/art.27642. PMID: 20617520. 18: Wang S, Li B, Shen X, Duan H, Guo Z, Li X, Sun F. The cannabinoid receptor CB1 affects the proliferation and apoptosis of adenomyotic human uterine smooth muscle cells of the junctional zone: a mechanism study. Reprod Biol Endocrinol. 2021 Feb 2;19(1):16. doi: 10.1186/s12958-020-00690-0. PMID: 33531043; PMCID: PMC7852156. 19: Kenessey I, Bánki B, Márk A, Varga N, Tóvári J, Ladányi A, Rásó E, Tímár J. Revisiting CB1 receptor as drug target in human melanoma. Pathol Oncol Res. 2012 Oct;18(4):857-66. doi: 10.1007/s12253-012-9515-y. Epub 2012 Mar 24. PMID: 22447182. 20: Wang ZY, McDowell T, Wang P, Alvarez R, Gomez T, Bjorling DE. Activation of CB1 inhibits NGF-induced sensitization of TRPV1 in adult mouse afferent neurons. Neuroscience. 2014 Sep 26;277:679-89. doi: 10.1016/j.neuroscience.2014.07.041. Epub 2014 Aug 1. PMID: 25088915; PMCID: PMC4626020.