Histidine methyl ester

Names
Other names

Methyl L-histidinate, HME

Identifiers

CAS Number

* 1499-46-3 Y
* 7389-87-9 (HCl) N

3D model (JSmol)

* Interactive image

Beilstein Reference

| 957974
ChEBI |

* CHEBI:70961

ChEMBL |

* ChEMBL54664

ChemSpider |

* 83857

ECHA InfoCard | 100.014.645
EC Number |

* 216-109-3

PubChem CID

* 92893

UNII |

* 9IHZ1723UE Y

CompTox Dashboard (EPA)

* DTXSID90933797

InChI

* InChI=1S/C7H11N3O2/c1-12-7(11)6(8)2-5-3-9-4-10-5/h3-4,6H,2,8H2,1H3,(H,9,10)/t6-/m0/s1

Key: BXRMEWOQUXOLDH-LURJTMIESA-N

SMILES

* COC(=O)[C@H](Cc1c[nH]cn1)N

Properties

Chemical formula

| C7H11N3O2
Molar mass | 169.184 g·mol−1

Except where otherwise noted, data are given for materials in their standard state (at 25 °C [77 °F], 100 kPa).

Infobox references

Chemical compound

Histidine methyl ester (HME) is an irreversible histidine decarboxylase inhibitor.[1][2][3] It is the methyl ester of histidine.

HME bound to histidine decarboxylase

## See also

[edit]

* Histidine decarboxylase
* α-Fluoromethylhistidine

## References

[edit]

1. ^ Lane, Roger S; Manning, James M; Snell, Esmond E (2002). "Histidine decarboxylase of lactobacillus 30a: inactivation and active-site labeling by L-histidine methyl ester". Biochemistry. 15 (19): 4180–5\. doi:10.1021/bi00664a008. PMID 963031.4180-5&rft.date=2002&rft_id=info:doi/10.1021/bi00664a008&rft_id=info:pmid/963031&rft.aulast=Lane&rft.aufirst=Roger+S&rft.au=Manning,+James+M&rft.au=Snell,+Esmond+E&rfr_id=info:sid/en.wikipedia.org:Histidine+methyl+ester" class="Z3988">
2. ^ Alston, Theodore A; Abeles, Robert H (2002). "Reaction of Lactobacillus histidine decarboxylase with L-histidine methyl ester". Biochemistry. 26 (13): 4082–5\. doi:10.1021/bi00387a051. PMID 3651438.4082-5&rft.date=2002&rft_id=info:doi/10.1021/bi00387a051&rft_id=info:pmid/3651438&rft.aulast=Alston&rft.aufirst=Theodore+A&rft.au=Abeles,+Robert+H&rfr_id=info:sid/en.wikipedia.org:Histidine+methyl+ester" class="Z3988">
3. ^ Komori, H; Nitta, Y; Ueno, H; Higuchi, Y (2012). "Structural Study Reveals That Ser-354 Determines Substrate Specificity on Human Histidine Decarboxylase". The Journal of Biological Chemistry. 287 (34): 29175–83\. doi:10.1074/jbc.M112.381897. PMC 3436558. PMID 22767596.29175-83&rft.date=2012&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3436558#id-name=PMC&rft_id=info:pmid/22767596&rft_id=info:doi/10.1074/jbc.M112.381897&rft.aulast=Komori&rft.aufirst=H&rft.au=Nitta,+Y&rft.au=Ueno,+H&rft.au=Higuchi,+Y&rft_id=https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3436558&rfr_id=info:sid/en.wikipedia.org:Histidine+methyl+ester" class="Z3988">

* v
* t
* e

Monoamine metabolism modulators

Non-specific|

| AAADTooltip Aromatic L-amino acid decarboxylase|

* Substrates→Products: L-DOPA (levodopa)→Dopamine
* 5-HTP→Serotonin
* L-Histidine→Histamine
* Phenylalanine→Phenethylamine
* L-Tyrosine→Tyramine
* Tryptophan→Tryptamine

* Inhibitors: Benserazide
* Carbidopa
* DFMD
* Genistein
* Methyldopa

|

MAOTooltip Monoamine oxidase|

* Substrates→Products (with ALDHTooltip Aldehyde dehydrogenase/ALRTooltip ALR): Epinephrine (adrenaline)→DHMA
* Metanephrine→MHPG/VMA
* Norepinephrine (noradrenaline)→DHMA
* Normetanephrine→MHPG/VMA
* Dopamine→DOPAC
* 3-Methoxytyramine→HVA
* Serotonin→5-HIAA

* Inhibitors: Non-selective: Benmoxin
* Caroxazone
* Echinopsidine
* Furazolidone
* Guineesine
* Hydralazine
* Indantadol
* Iproclozide
* Iproniazid
* Isocarboxazid
* Isoniazid
* Linezolid
* Mebanazine
* Metfendrazine
* Nialamide
* Octamoxin
* Paraxazone
* Phenelzine
* Pheniprazine
* Phenoxypropazine
* Pivhydrazine
* Procarbazine
* Safrazine
* Tranylcypromine

* Inhibitors: MAO-A-selective: Amiflamine
* Bazinaprine
* Befloxatone
* Brofaromine
* Cimoxatone
* Clorgiline
* CX157 (Tyrima)
* Eprobemide
* Esuprone
* Harmala alkaloids (e.g., harmine, harmaline, harman, norharman, tetrahydroharmine)
* Methylene blue
* Metralindole
* Minaprine
* Moclobemide
* Pirlindole
* Sercloremine
* Tetrindole
* Toloxatone

* Inhibitors: MAO-B selective: Adarigiline
* Almoxatone
* D-Deprenyl
* Desmethylselegiline
* Ethanol
* Ladostigil
* Lazabemide
* Milacemide
* Mofegiline
* Nicotine
* Pargyline‡
* Rasagiline
* Safinamide
* Selegiline (L-Deprenyl)
* Sembragiline
* Tisolagiline
* Vafidemstat

Phenethylamines
(dopamine, epinephrine,
norepinephrine)|

| PAHTooltip Phenylalanine hydroxylase|

* Substrates→Products: Phenylalanine→Tyrosine

* Inhibitors: 3,4-Dihydroxystyrene
* α-Methylphenylalanine

|

THTooltip Tyrosine hydroxylase|

* Substrates→Products: Tyrosine→L-DOPA (levodopa)

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* 3-Iodotyrosine
* α-Methyl-5-hydroxytryptophan (α-Me-5-HTP)
* α-Methylphenylalanine
* Aquayamycin
* Bulbocapnine
* Methyldopa (α-methyl-L-DOPA)
* Metirosine (α-methyl-p-tyrosine)
* Oudenone

DBHTooltip Dopamine beta-hydroxylase|

* Substrates→Products: Dopamine→Norepinephrine (Noradrenaline)

* Inhibitors: Bupicomide
* Disulfiram
* Dopastin
* Etamicastat
* Fusaric acid
* Nepicastat
* Phenopicolinic acid
* Tropolone
* Zamicastat

PNMTTooltip Phenylethanolamine N-methyltransferase|

* Substrates→Products: Norepinephrine (noradrenaline)→Epinephrine (adrenaline)

* Inhibitors: CGS-19281A
* SKF-64139
* SKF-7698

COMTTooltip Catechol-O-methyl transferase|

* Substrates→Products: Dopamine→3-Methoxytyramine
* DOPAC→Homovanillic acid
* Norepinephrine→Normetanephrine
* Epinephrine→Metanephrine
* DOPEG→MOPEG
* DOMA→VMA
* 2-Hydroxyestradiol→2-Methoxyestradiol
* 2-Hydroxyestrone→2-Methoxyestrone
* 4-Hydroxyestradiol→4-Methoxyestradiol
* 4-Hydroxyestrone→4-Methoxyestrone

* Inhibitors: 2-Hydroxyestradiol
* 2-Hydroxyestrone
* Entacapone
* Nebicapone
* Neluxicapone
* Nitecapone
* Opicapone
* Quinalizarin
* Tolcapone

Tryptamines
(serotonin, melatonin)|

| TPHTooltip Tryptophan hydroxylase|

* Substrates→Products: Tryptophan→5-HTP

* Inhibitors: AGN-2979
* Fenclonine (PCPA)
* Telotristat ethyl

|

AANATTooltip Serotonin N-acetyl transferase|

* Substrates→Products: Serotonin→N-Acetylserotonin

ASMTTooltip Acetylserotonin O-methyltransferase|

* Substrates→Products: N-Acetylserotonin→Melatonin

Histamine|

| HDCTooltip Histidine decarboxylase|

* Substrates→Products: L-Histidine→Histamine

* Inhibitors: Catechin
* Alpha-Fluoromethylhistidine
* Histidine methyl ester
* Meciadanol
* Naringenin
* Tritoqualine

|

HNMTTooltip Histamine N-methyltransferase|

* Substrates→Products: Histamine→N-Methylhistamine

* Inhibitors: Amodiaquine
* Diphenhydramine
* Harmaline
* Metoprine
* Quinacrine
* SKF-91488
* Tacrine

DAOTooltip Diamine oxidase|

* Substrates→Products: Histamine→Imidazole acetic acid

* Inhibitors: Pimagedine (aminoguanidine)

See also: Receptor/signaling modulators • Adrenergics • Dopaminergics • Melatonergics • Serotonergics • Monoamine reuptake inhibitors • Monoamine releasing agents • Monoamine neurotoxins

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* e

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*[CID]: Compound ID
*[EPA]: U.S. Environmental Protection Agency
*[v]: View this template
*[t]: Discuss this template
*[e]: Edit this template
*[AAAD]: Aromatic L-amino acid decarboxylase
*[MAO]: Monoamine oxidase
*[ALDH]: Aldehyde dehydrogenase
*[ALR]: Aldehyde reductase
*[PAH]: Phenylalanine hydroxylase
*[TH]: Tyrosine hydroxylase
*[DBH]: Dopamine beta-hydroxylase
*[PNMT]: Phenylethanolamine N-methyltransferase
*[COMT]: Catechol-O-methyl transferase
*[TPH]: Tryptophan hydroxylase
*[AANAT]: Serotonin N-acetyl transferase
*[ASMT]: Acetylserotonin O-methyltransferase
*[HDC]: Histidine decarboxylase
*[HNMT]: Histamine N-methyltransferase
*[DAO]: Diamine oxidase