(S)-alpha-Fluoromethylhistidine HCl
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MedKoo CAT#: 525854

CAS#: 81839-27-2 (HCl)

Description: (S)-alpha-Fluoromethylhistidine HCl is a potent irreversible histidine decarboxylase (HDC) inhibitor and glutathione S-transferase inhibitor. a-FMH was demonstrated to be an effective inhibitor of GST at micromolar concentration, suggesting that off-target effects of a-FMH may limit physiological drug metabolism and elimination by GST-dependent mechanisms.

Chemical Structure

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(S)-alpha-Fluoromethylhistidine HCl
CAS# 81839-27-2 (HCl)
Product data Instruction

Theoretical Analysis

MedKoo Cat#: 525854
Name: (S)-alpha-Fluoromethylhistidine HCl
CAS#: 81839-27-2 (HCl)
Chemical Formula: C7H12Cl2FN3O2
Exact Mass: 187.08
Molecular Weight: 260.090
Elemental Analysis: C, 32.33; H, 4.65; Cl, 27.26; F, 7.30; N, 16.16; O, 12.30

Price and Availability

Size Price Availability Quantity
2mg USD 160 Ready to ship
5mg USD 350 Ready to ship
10mg USD 550 Ready to ship
25mg USD 1050 Ready to ship
50mg USD 1850 Ready to ship
100mg USD 3250 Ready to ship
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Related CAS #: 73804-75-8 (free base)   81839-27-2 (HCl)  

Synonym: α-Fluoromethyl-L-histidine dihydrochloride; a-FMH; alpha-FMH; (S)-alpha-Fluoromethylhistidine 2HCl; (S)-alpha-Fluoromethylhistidine HCl; (S)-alpha-Fluoromethylhistidine dihydrochloride

IUPAC/Chemical Name: (S)-2-Amino-2-(fluoromethyl)-3-(1H-imidazol-5-yl)propanoic acid dihydrochloride

InChi Key: LIJUCORJKQZTOS-XCUBXKJBSA-N

InChi Code: InChI=1S/C7H10FN3O2.2ClH/c8-3-7(9,6(12)13)1-5-2-10-4-11-5;;/h2,4H,1,3,9H2,(H,10,11)(H,12,13);2*1H/t7-;;/m1../s1

SMILES Code: O=C(O)[C@@](CF)(N)CC1=CN=CN1.[H]Cl.[H]Cl

Appearance: Solid powder (highly hydroscopic powder. It may quickly become sticky solid powder in air, which would not impact the quality).

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: alpha-FMH is a desired product with implications for the study of histidine metabolism, the examination of the effects of depleted histamine levels, and the development of novel pharmaceutical and diagnostic agents.

Biological target: TBD
In vitro activity: Addition of 10 mM PABA was observed to limit glutathione transferase activity to 33 ± 3.9% that of the uninhibited enzyme. Notably, addition of 150 μM α-FMH (alpha-Fluoromethylhistidine) (equivalent to approximately 1/70th the amount of PABA input) was sufficient to limit glutathione transferase activity to 57 ± 8.7% of the uninhibited enzyme. As micromolar concentrations of α-FMH were sufficient to significantly limit glutathione transfer activity, this study concludes that α-FMH is a potent GST inhibitor, consistent with predictions from this study’s in silico analysis. Reference: Bioorg Med Chem Lett. 2017 Mar 15;27(6):1335-1340. https://pubmed.ncbi.nlm.nih.gov/28228363/
In vivo activity: The results show that orexin-B significantly (p < 0.05) increased wakefulness during the infusion period and that α-FMH (alpha-Fluoromethylhistidine) significantly (p < 0.05) blocked this effect of orexin in rats. Regarding non-REM sleep, the results showed that orexin significantly decreased this sleep stage and that this orexin-B effect was blocked with prior administration of α-FMH. Fig. 2 presents further analysis regarding the total time spent during the 5-h infusion of orexin-B (10 nmol) and the influence of α-FMH on the effect of orexin-B for wakefulness [F(2,23) = 213.25, p = 0.0001], non-REM sleep [F(2,23) = 51.10, p = 0.0001], and REM sleep [F(2,23) = 19.25, p = 0.0001], respectively. Reference: Behav Brain Res. 2010 Feb 11;207(1):151-4. https://pubmed.ncbi.nlm.nih.gov/19818811/

Preparing Stock Solutions

The following data is based on the product molecular weight 260.09 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. Considine KL, Stefanidis L, Grozinger KG, Audie J, Alper BJ. Efficient synthesis of α-fluoromethylhistidine di-hydrochloride and demonstration of its efficacy as a glutathione S-transferase inhibitor. Bioorg Med Chem Lett. 2017 Mar 15;27(6):1335-1340. doi: 10.1016/j.bmcl.2017.02.024. Epub 2017 Feb 14. PMID: 28228363. 2. Yu J, Fang Q, Lou GD, Shou WT, Yue JX, Tang YY, Hou WW, Xu TL, Ohtsu H, Zhang SH, Chen Z. Histamine modulation of acute nociception involves regulation of Nav 1.8 in primary afferent neurons in mice. CNS Neurosci Ther. 2013 Sep;19(9):649-58. doi: 10.1111/cns.12134. Epub 2013 Jun 15. PMID: 23773488; PMCID: PMC6493618. 3. Yasuko S, Atanda AM, Masato M, Kazuhiko Y, Kazuki H. Alpha-fluoromethylhistidine, a histamine synthesis inhibitor, inhibits orexin-induced wakefulness in rats. Behav Brain Res. 2010 Feb 11;207(1):151-4. doi: 10.1016/j.bbr.2009.09.049. Epub 2009 Oct 8. PMID: 19818811.
In vitro protocol: 1. Considine KL, Stefanidis L, Grozinger KG, Audie J, Alper BJ. Efficient synthesis of α-fluoromethylhistidine di-hydrochloride and demonstration of its efficacy as a glutathione S-transferase inhibitor. Bioorg Med Chem Lett. 2017 Mar 15;27(6):1335-1340. doi: 10.1016/j.bmcl.2017.02.024. Epub 2017 Feb 14. PMID: 28228363.
In vivo protocol: 1. Yu J, Fang Q, Lou GD, Shou WT, Yue JX, Tang YY, Hou WW, Xu TL, Ohtsu H, Zhang SH, Chen Z. Histamine modulation of acute nociception involves regulation of Nav 1.8 in primary afferent neurons in mice. CNS Neurosci Ther. 2013 Sep;19(9):649-58. doi: 10.1111/cns.12134. Epub 2013 Jun 15. PMID: 23773488; PMCID: PMC6493618. 2. Yasuko S, Atanda AM, Masato M, Kazuhiko Y, Kazuki H. Alpha-fluoromethylhistidine, a histamine synthesis inhibitor, inhibits orexin-induced wakefulness in rats. Behav Brain Res. 2010 Feb 11;207(1):151-4. doi: 10.1016/j.bbr.2009.09.049. Epub 2009 Oct 8. PMID: 19818811.

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1: Bencsáth M, Pálóczi K, Szalai C, Szenthe A, Szeberényi J, Falus A. Histidine decarboxylase in peripheral lymphocytes of healthy individuals and chronic lymphoid leukemia patients. Pathol Oncol Res. 1998;4(2):121-4. PubMed PMID: 9654597.

2: Vaziri P, Dang K, Anderson GH. Evidence for histamine involvement in the effect of histidine loads on food and water intake in rats. J Nutr. 1997 Aug;127(8):1519-26. PubMed PMID: 9237947.

3: Malmberg-Aiello P, Lamberti C, Ghelardini C, Giotti A, Bartolini A. Role of histamine in rodent antinociception. Br J Pharmacol. 1994 Apr;111(4):1269-79. PubMed PMID: 8032614; PubMed Central PMCID: PMC1910136.

4: Brandes LJ, Davie JR, Paraskevas F, Sukhu B, Bogdanovic RP, LaBella FS. The antiproliferative potency of histamine antagonists correlates with inhibition of binding of [3H]-histamine to novel intracellular receptors (HIC) in microsomal and nuclear fractions of rat liver. Agents Actions Suppl. 1991;33:325-42. PubMed PMID: 2053513.

5: Saxena SP, McNicol A, Brandes LJ, Becker AB, Gerrard JM. A role for intracellular histamine in collagen-induced platelet aggregation. Blood. 1990 Jan 15;75(2):407-14. PubMed PMID: 2104768.