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MedKoo Cat#: 329862 | Name: Guvacine free base

Description:

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

Guvacine is a GABA uptake inhibitor. Guvacine competitively inhibits GABA uptake (IC50 = 10 μM; Ki = 14 μM) in rat hippocampal brain slices.

Chemical Structure

Guvacine free base
Guvacine free base
CAS#498-96-4 (free base)

Theoretical Analysis

MedKoo Cat#: 329862

Name: Guvacine free base

CAS#: 498-96-4 (free base)

Chemical Formula: C6H9NO2

Exact Mass: 127.0600

Molecular Weight: 127.14

Elemental Analysis: C, 56.68; H, 7.14; N, 11.02; O, 25.17

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 #
498-96-4 (free base) 6197-39-3 (Norarecoline HCl) 6027-91-4 (HCl)
Synonym
Guvacine free base; Guvacoline;
IUPAC/Chemical Name
1,2,5,6-Tetrahydropyridine-3-carboxylic acid
InChi Key
QTDZOWFRBNTPQR-UHFFFAOYSA-N
InChi Code
InChI=1S/C6H9NO2/c8-6(9)5-2-1-3-7-4-5/h2,7H,1,3-4H2,(H,8,9)
SMILES Code
O=C(C1=CCCNC1)O
Appearance
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

Preparing Stock Solutions

The following data is based on the product molecular weight 127.14 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
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Effects of the Areca nut constituents arecaidine and guvacine on the action of GABA in the cat central nervous system. Brain Res. 1977 Nov 18;136(3):513-22. PubMed PMID: 922499. 5: Knutsen LJ, Andersen KE, Lau J, Lundt BF, Henry RF, Morton HE, Naerum L, Petersen H, Stephensen H, Suzdak PD, Swedberg MD, Thomsen C, Sørensen PO. Synthesis of novel GABA uptake inhibitors. 3. Diaryloxime and diarylvinyl ether derivatives of nipecotic acid and guvacine as anticonvulsant agents. J Med Chem. 1999 Sep 9;42(18):3447-62. PubMed PMID: 10479278. 6: McELVAIN SM, STORK G. Piperidine derivatives; the preparation of l-benzoyl-3-carbethoxy-4-piperidone; a synthesis of guvacine. J Am Chem Soc. 1946 Jun;68:1049-53. PubMed PMID: 20985618. 7: Voigt V, Laug L, Zebisch K, Thondorf I, Markwardt F, Brandsch M. Transport of the areca nut alkaloid arecaidine by the human proton-coupled amino acid transporter 1 (hPAT1). J Pharm Pharmacol. 2013 Apr;65(4):582-90. doi: 10.1111/jphp.12006. Epub 2012 Nov 19. PubMed PMID: 23488788. 8: Yu H, Tang L, Wu H, Wang K, Cai B, Zhang X, Zhang C, Yin Y. Determination of contents of four alkaloids in Pericarpium arecae by quantitative analysis of multi-components by single-marker. Pak J Pharm Sci. 2016 Jul;29(4):1269-74. PubMed PMID: 27393441. 9: Larsson OM, Falch E, Krogsgaard-Larsen P, Schousboe A. Kinetic characterization of inhibition of gamma-aminobutyric acid uptake into cultured neurons and astrocytes by 4,4-diphenyl-3-butenyl derivatives of nipecotic acid and guvacine. J Neurochem. 1988 Mar;50(3):818-23. PubMed PMID: 3339356. 10: Srimany A, George C, Naik HR, Pinto DG, Chandrakumar N, Pradeep T. Developmental patterning and segregation of alkaloids in areca nut (seed of Areca catechu) revealed by magnetic resonance and mass spectrometry imaging. Phytochemistry. 2016 May;125:35-42. doi: 10.1016/j.phytochem.2016.02.002. Epub 2016 Feb 17. PubMed PMID: 26896852. 11: Mantegazza P, Tammiso R, Vicentini L, Zambotti F, Zonta N. Nipecotic acid and guvacine antagonism on morphine analgesia in rats. Pharmacol Res Commun. 1979 Sep;11(8):657-62. PubMed PMID: 515113. 12: Yu HL, Tang LJ, Wu H, Mao CQ, Lu TL, Mao SH. [Optimization of Preparation of Cutting-processed Arecae Pericarpium with Multi-index Orthogonal Method]. Zhong Yao Cai. 2014 Dec;37(12):2178-81. Chinese. PubMed PMID: 26080498. 13: Jaw SP, Nguyen B, Vuong QT, Trinh TA, Nguyen M, Truong DD. Effects of GABA uptake inhibitors on posthypoxic myoclonus in rats. Brain Res Bull. 1996;39(3):189-92. PubMed PMID: 8866696. 14: Rasmussen RN, Lagunas C, Plum J, Holm R, Nielsen CU. Interaction of GABA-mimetics with the taurine transporter (TauT, Slc6a6) in hyperosmotic treated Caco-2, LLC-PK1 and rat renal SKPT cells. Eur J Pharm Sci. 2016 Jan 20;82:138-46. doi: 10.1016/j.ejps.2015.11.020. Epub 2015 Nov 26. PubMed PMID: 26631583. 15: Yuan J, Yang D, Liang Y, Gao W, Ren Z, Zeng W, Wang B, Han J, Guo D. Alkaloids from areca (betel) nuts and their effects on human sperm motility in vitro. J Food Sci. 2012 Apr;77(4):T70-8. doi: 10.1111/j.1750-3841.2012.02653.x. PubMed PMID: 22515256. 16: Franke AA, Li X, Lai JF. Pilot study of the pharmacokinetics of betel nut and betel quid biomarkers in saliva, urine, and hair of betel consumers. Drug Test Anal. 2016 Oct;8(10):1095-1099. doi: 10.1002/dta.1912. Epub 2015 Dec 1. PubMed PMID: 26619803; PubMed Central PMCID: PMC4967029. 17: Franke AA, Mendez AJ, Lai JF, Arat-Cabading C, Li X, Custer LJ. Composition of betel specific chemicals in saliva during betel chewing for the identification of biomarkers. Food Chem Toxicol. 2015 Jun;80:241-6. doi: 10.1016/j.fct.2015.03.012. Epub 2015 Mar 19. PubMed PMID: 25797484; PubMed Central PMCID: PMC4454402. 18: Chattopadhyay A, Ray JG. Molecular Pathology of Malignant Transformation of Oral Submucous Fibrosis. J Environ Pathol Toxicol Oncol. 2016;35(3):193-205. Review. PubMed PMID: 27910776. 19: Virmani MA, Conti R, Spadoni A, Rossi S, Arrigoni-Martelli E. Inhibition of L-carnitine uptake into primary rat cortical cell cultures by GABA and GABA uptake blockers. Pharmacol Res. 1995 Mar-Apr;31(3-4):211-5. PubMed PMID: 7630861. 20: Kern FT, Wanner KT. Generation and screening of oxime libraries addressing the neuronal GABA transporter GAT1. ChemMedChem. 2015 Feb;10(2):396-410. doi: 10.1002/cmdc.201402376. Epub 2014 Nov 4. PubMed PMID: 25369775.