L-368899 free base

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MedKoo CAT#: 596538

CAS#: 148927-60-0 (free Base)

Description: L-368899 is a potent, non-peptide and orally active oxytocin receptor antagonist (IC50 = 8.9 nM) that displays > 40-fold selectivity over vasopressin V1a and V2 receptors (IC50 values are 370 and 570 nM respectively). L-368,899 HCl antagonizes oxytocin-induced uterine contractions in vitro and in vivo.


Price and Availability

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Pricing updated 2020-03-30. Prices are subject to change without notice.

L 368899 (Free base) is not in stock, may be available through custom synthesis. For cost-effective reason, minimum 1 gram order is requested. The product will be characterized by NMR, HPLC and MS analysis. Purity (HPLC) is usually >98%. CoA, QC data, MSDS will be provided when product is successfully made. The estimated lead time is 2-3 months. Please send email to sales@medkoo.com to inquire quote.


Chemical Structure

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Theoretical Analysis

MedKoo Cat#: 596538
Name: L-368899 free base
CAS#: 148927-60-0 (free Base)
Chemical Formula: C26H42N4O5S2
Exact Mass: 554.2597
Molecular Weight: 554.76
Elemental Analysis: C, 56.29; H, 7.63; N, 10.10; O, 14.42; S, 11.56


Related CAS #: 160312-62-9 (HCl)   148927-60-0 (free Base)  

Synonym: L 368899; L-368899; L368899; L-368,899; L 368,899; L368,899;

IUPAC/Chemical Name: (2R)-2-amino-N-((1R,4R)-7,7-dimethyl-1-(((4-(o-tolyl)piperazin-1-yl)sulfonyl)methyl)bicyclo[2.2.1]heptan-2-yl)-4-(methylsulfonyl)butanamide

InChi Key: MWIASLNTAGRGGA-OGUNDUEHSA-N

InChi Code: InChI=1S/C26H42N4O5S2/c1-19-7-5-6-8-22(19)29-12-14-30(15-13-29)37(34,35)18-26-11-9-20(25(26,2)3)17-23(26)28-24(31)21(27)10-16-36(4,32)33/h5-8,20-21,23H,9-18,27H2,1-4H3,(H,28,31)/t20-,21-,23?,26+/m1/s1

SMILES Code: O=C(NC1[C@@](C2(C)C)(CS(=O)(N3CCN(C4=CC=CC=C4C)CC3)=O)CC[C@]2([H])C1)[C@H](N)CCS(=O)(C)=O


Technical Data

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


References

1: Kang SW, Jayanthi S, Nagarajan G, Suresh Kumar TK, Kuenzel WJ. Identification of avian vasotocin receptor subtype-specific antagonists involved in the stress response of the chicken, Gallus gallus. J Biomol Struct Dyn. 2018 May 17:1-15. doi: 10.1080/07391102.2018.1464957. [Epub ahead of print] PubMed PMID: 29658387.

2: Kotani M, Shimono K, Yoneyama T, Nakako T, Matsumoto K, Ogi Y, Konoike N, Nakamura K, Ikeda K. An eye tracking system for monitoring face scanning patterns reveals the enhancing effect of oxytocin on eye contact in common marmosets. Psychoneuroendocrinology. 2017 Sep;83:42-48. doi: 10.1016/j.psyneuen.2017.05.009. Epub 2017 May 10. PubMed PMID: 28586711.

3: Taylor JH, Cavanaugh J, French JA. Neonatal oxytocin and vasopressin manipulation alter social behavior during the juvenile period in Mongolian gerbils. Dev Psychobiol. 2017 Jul;59(5):653-657. doi: 10.1002/dev.21533. Epub 2017 May 31. PubMed PMID: 28561891; PubMed Central PMCID: PMC5523843.

4: Boulet NP, Cloutier CJ, Ossenkopp KP, Kavaliers M. Oxytocin, social factors, and the expression of conditioned disgust (anticipatory nausea) in male rats. Behav Pharmacol. 2016 Dec;27(8):718-725. PubMed PMID: 27740965.

5: Zimmermann FF, Gaspary KV, Siebel AM, Bonan CD. Oxytocin reversed MK-801-induced social interaction and aggression deficits in zebrafish. Behav Brain Res. 2016 Sep 15;311:368-374. doi: 10.1016/j.bbr.2016.05.059. Epub 2016 May 28. PubMed PMID: 27247142.

6: Herisson FM, Waas JR, Fredriksson R, Schiöth HB, Levine AS, Olszewski PK. Oxytocin Acting in the Nucleus Accumbens Core Decreases Food Intake. J Neuroendocrinol. 2016 Apr;28(4). doi: 10.1111/jne.12381. PubMed PMID: 27114001.

7: Lee SY, Park SH, Chung C, Kim JJ, Choi SY, Han JS. Oxytocin Protects Hippocampal Memory and Plasticity from Uncontrollable Stress. Sci Rep. 2015 Dec 21;5:18540. doi: 10.1038/srep18540. PubMed PMID: 26688325; PubMed Central PMCID: PMC4685249.

8: Wei D, Lee D, Cox CD, Karsten CA, Peñagarikano O, Geschwind DH, Gall CM, Piomelli D. Endocannabinoid signaling mediates oxytocin-driven social reward. Proc Natl Acad Sci U S A. 2015 Nov 10;112(45):14084-9. doi: 10.1073/pnas.1509795112. Epub 2015 Oct 26. PubMed PMID: 26504214; PubMed Central PMCID: PMC4653148.

9: Hagen E, Shprung D, Minakova E, Washington J 3rd, Kumar U, Shin D, Sankar R, Mazarati A. Autism-Like Behavior in BTBR Mice Is Improved by Electroconvulsive Therapy. Neurotherapeutics. 2015 Jul;12(3):657-66. doi: 10.1007/s13311-015-0357-7. PubMed PMID: 25916397; PubMed Central PMCID: PMC4489959.

10: Olszewski PK, Allen K, Levine AS. Effect of oxytocin receptor blockade on appetite for sugar is modified by social context. Appetite. 2015 Mar;86:81-7. doi: 10.1016/j.appet.2014.10.007. Epub 2014 Oct 22. PubMed PMID: 25453587.

11: Calcagnoli F, Stubbendorff C, Meyer N, de Boer SF, Althaus M, Koolhaas JM. Oxytocin microinjected into the central amygdaloid nuclei exerts anti-aggressive effects in male rats. Neuropharmacology. 2015 Mar;90:74-81. doi: 10.1016/j.neuropharm.2014.11.012. Epub 2014 Nov 29. PubMed PMID: 25437825.

12: Kuteykin-Teplyakov K, Maldonado R. Looking for prosocial genes: ITRAQ analysis of proteins involved in MDMA-induced sociability in mice. Eur Neuropsychopharmacol. 2014 Nov;24(11):1773-83. doi: 10.1016/j.euroneuro.2014.08.007. Epub 2014 Aug 27. PubMed PMID: 25241352.

13: Cavanaugh J, Mustoe AC, Taylor JH, French JA. Oxytocin facilitates fidelity in well-established marmoset pairs by reducing sociosexual behavior toward opposite-sex strangers. Psychoneuroendocrinology. 2014 Nov;49:1-10. doi: 10.1016/j.psyneuen.2014.06.020. Epub 2014 Jul 3. PubMed PMID: 25038478; PubMed Central PMCID: PMC4165758.

14: Olszewski PK, Ulrich C, Ling N, Allen K, Levine AS. A non-peptide oxytocin receptor agonist, WAY-267,464, alleviates novelty-induced hypophagia in mice: insights into changes in c-Fos immunoreactivity. Pharmacol Biochem Behav. 2014 Sep;124:367-72. doi: 10.1016/j.pbb.2014.07.007. Epub 2014 Jul 17. PubMed PMID: 25038444.

15: Herisson FM, Brooks LL, Waas JR, Levine AS, Olszewski PK. Functional relationship between oxytocin and appetite for carbohydrates versus saccharin. Neuroreport. 2014 Aug 20;25(12):909-14. doi: 10.1097/WNR.0000000000000201. PubMed PMID: 24893201.

16: Qiu F, Qiu CY, Cai H, Liu TT, Qu ZW, Yang Z, Li JD, Zhou QY, Hu WP. Oxytocin inhibits the activity of acid-sensing ion channels through the vasopressin, V1A receptor in primary sensory neurons. Br J Pharmacol. 2014 Jun;171(12):3065-76. doi: 10.1111/bph.12635. PubMed PMID: 24641084; PubMed Central PMCID: PMC4055206.

17: Mooney SJ, Douglas NR, Holmes MM. Peripheral administration of oxytocin increases social affiliation in the naked mole-rat (Heterocephalus glaber). Horm Behav. 2014 Apr;65(4):380-5. doi: 10.1016/j.yhbeh.2014.02.003. Epub 2014 Feb 13. PubMed PMID: 24530845.

18: Olszewski PK, Waas JR, Brooks LL, Herisson F, Levine AS. Oxytocin receptor blockade reduces acquisition but not retrieval of taste aversion and blunts responsiveness of amygdala neurons to an aversive stimulus. Peptides. 2013 Dec;50:36-41. doi: 10.1016/j.peptides.2013.09.008. Epub 2013 Sep 21. PubMed PMID: 24063812.

19: Mullis K, Kay K, Williams DL. Oxytocin action in the ventral tegmental area affects sucrose intake. Brain Res. 2013 Jun 4;1513:85-91. doi: 10.1016/j.brainres.2013.03.026. Epub 2013 Mar 30. PubMed PMID: 23548602; PubMed Central PMCID: PMC3739708.

20: Smith AL, Freeman SM, Voll RJ, Young LJ, Goodman MM. Carbon-11 N-methyl alkylation of L-368,899 and in vivo PET imaging investigations for neural oxytocin receptors. Bioorg Med Chem Lett. 2013 Feb 1;23(3):902-6. doi: 10.1016/j.bmcl.2012.10.116. Epub 2012 Nov 17. PubMed PMID: 23270988; PubMed Central PMCID: PMC3756487.