Page last updated: 2024-11-04

racemetirosine

Description Research Excerpts Clinical Trials Roles Classes Pathways Study Profile Bioassays Related Drugs Related Conditions Protein Interactions Research Growth Market Indicators

Description

Racemetirosine, also known as DL-tyrosine, is a racemic mixture of the L- and D-enantiomers of tyrosine. It is a non-essential amino acid that plays a role in the synthesis of neurotransmitters like dopamine, norepinephrine, and epinephrine. Racemetirosine has been studied for its potential therapeutic effects in conditions such as depression, anxiety, and fatigue. Its synthesis typically involves racemization of L-tyrosine, a process that can be achieved through chemical or enzymatic methods. While L-tyrosine is the primary form found in the body and used in protein synthesis, racemetirosine offers a potential alternative source of tyrosine for various physiological functions. Research into racemetirosine continues to explore its potential benefits and applications, including its role in cognitive enhancement and athletic performance.'
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alpha-Methyltyrosine: An inhibitor of the enzyme TYROSINE 3-MONOOXYGENASE, and consequently of the synthesis of catecholamines. It is used to control the symptoms of excessive sympathetic stimulation in patients with PHEOCHROMOCYTOMA. (Martindale, The Extra Pharmacopoeia, 30th ed) [Medical Subject Headings (MeSH), National Library of Medicine, extracted Dec-2023]

Cross-References

ID SourceID
PubMed CID3125
CHEMBL ID1330596
SCHEMBL ID61871
MeSH IDM0373730

Synonyms (107)

Synonym
AKOS003391424
smr000059140
MLS000028638
dl-alpha-methyl-p-tyrosine
EU-0100001
alpha-methyl-dl-tyrosine, 98%
LOPAC0_000001
658-48-0
alpha-methyltyrosine
alpha-methyl-p-tyrosine
ampt
STK272180
racemetirosina [inn-spanish]
(+-)-alpha-methyl-dl-tyrosine
alpha-methylparatyrosine, dl-
tyrosine, alpha-methyl-
racemetirosine [inn]
einecs 211-523-0
dl-alpha-methyltyrosine
(r,s)-2-amino-3-(4-hydroxyphenyl)-2-methylpropionsaeure
metyrosine, dl-
brn 2938704
ai3-62542
h 9/88
racemetirosinum [inn-latin]
racemetirosine
einecs 210-635-7
NCGC00093528-01
NCGC00093528-02
M-5185 ,
alpha-methyl-dl-tyrosine
NCGC00015701-03
4-hydroxy-alpha-methylphenylalanine
NCGC00015701-05
2-amino-3-(4-hydroxyphenyl)-2-methylpropanoic acid
HMS3260A03
CCG-204097
2-amino-3-(4-hydroxy-phenyl)-2-methyl-propionic acid
S9713
NCGC00015701-04
racemetyrosine
who 4292
unii-x88tto174z
4-14-00-02453 (beilstein handbook reference)
racemetirosina
racemetirosinum
sm-88
x88tto174z ,
racemetyrosine [usan]
620-30-4
FT-0632594
FT-0622266
LP00001
tyrosine, .alpha.-methyl-
racemetirosine [who-dd]
2-(4-hydroxybenzyl)-2-aminopropanoic acid
d,l-metyrosine
dnp-01
sm-88 component racemetyrosine
CHEMBL1330596
dl-metyrosine
.alpha.-methyl-p-tyrosine
dl-2-methyl-p-tyrosine
l1-79
2-p-hydroxyphenylmethyl-dl-alanine
gtpl5094
AKOS022063174
SCHEMBL61871
.alpha.-methyltyrosine
tox21_500001
NCGC00260686-01
a-methyl-dl-p-tyrosine
(.+/-.)-.alpha.-methyl-dl-tyrosine
NHTGHBARYWONDQ-UHFFFAOYSA-N
dl-.alpha.-methyl-p-tyrosine
2-methyltyrosine
dl-.alpha.-methyltyrosine
.alpha.-methyl-dl-tyrosine
.alpha.-methylparatyrosine
mfcd00004187
mfcd00064201
dl-2-methyl-3-(4-hydroxyphenyl)alanine
a-methyl-dl-tyrosine
alpha-methyl-dl-tyrosine, >=95% (nt)
CS-D0593
SR-01000075607-1
sr-01000075607
sr-01000075605
SR-01000075605-1
FT-0771147
DS-6468
SY099144
d,l-alpha-methyltyrosine
Q15408417
DTXSID90859529
racemetyrosine (sm-88)
SDCCGSBI-0049990.P002
NCGC00015701-07
D11606
racemetyrosine (usan)
SY045851
alpha -methyl-d,l-tyrosine
?-methyl-d,l-tyrosine
-methyl-p-tyrosine
2-amino-3-(4-hydroxyphenyl)-2-methylpropanoicacid
EN300-314129
HY-33549

Research Excerpts

Toxicity

ExcerptReferenceRelevance
"4 mg/kg - dose 1/4th of LD50 given ip), produced several autonomic, neurological and behavioral effects in mice with peak effects being at 15 min."( Acute neurobehavioural toxicity of phosphamindon and its drug-induced alteration.
Agarwal, AK; Sankaranarayanan, A; Sharma, PL, 1990
)
0.28
" These findings are in agreement with previous observations suggesting that manganese increases toxic products originating from dopamine catabolism."( Role of dopamine in manganese neurotoxicity.
Cappabianca, V; Groppetti, A; Parati, EA; Parenti, M; Rusconi, L, 1988
)
0.27
" To determine if the vesicular pool of DA was essential for the expression of METH-induced DA neurotoxicity, reserpine (3 mg/kg, given iintraperitoneally 24-26 h prior to METH) was given prior to a toxic dose regimen of METH."( Evidence against an essential role of endogenous brain dopamine in methamphetamine-induced dopaminergic neurotoxicity.
Callahan, BT; McCann, UD; Ricaurte, GA; Yuan, J, 2001
)
0.31
" It is known that dopamine (DA) enhances this toxic effect."( Endogenous dopamine enhances the neurotoxicity of 3-nitropropionic acid in the striatum through the increase of mitochondrial respiratory inhibition and free radicals production.
Cano, J; de Pablos, RM; Herrera, AJ; Machado, A; Navarro, A; Santiago, M; Tomás-Camardiel, M; Villarán, RF, 2008
)
0.35
" Sedation, anemia, and death were reported in 1 patient each as serious adverse drug reactions during the 24-week treatment."( Efficacy and safety of metyrosine in pheochromocytoma/paraganglioma: a multi-center trial in Japan.
Harada, T; Ichihara, A; Imai, T; Katabami, T; Kawata, N; Matsuda, T; Naruse, M; Nomura, M; Okamoto, T; Satoh, F; Takekoshi, K; Tanabe, A; Tanaka, T; Tsuiki, M; Yamada, M, 2018
)
0.48

Pharmacokinetics

ExcerptReferenceRelevance
" The possibility of a pharmacodynamic interaction involving neurotransmitters is also discussed."( Pharmacodynamic and pharmacokinetic interactions between alpha-methylparatyrosine and phenobarbitone.
Elhwuegi, AS, 1994
)
0.29

Compound-Compound Interactions

ExcerptReferenceRelevance
"The antipsychotic effect of alpha-methyltyrosine (alpha-MT) in combination with thioridazine was investigated by means of rating scales for "social behaviour" and "mental symptoms"."( Antipsychotic treatment with alpha-methyltyrosine in combination with thioridazine: prolactin response and interaction with dopaminergic precursor pools.
Carlsson, A; Larsson, M; Ohman, R; Wålinder, J; Wallin, L, 1984
)
0.27
" Unlike clozapine, neither the selective 5-HT2 receptor antagonist, ritanserin, nor the dopamine D2 receptor antagonists, haloperidol and remoxipride, caused locomotor activation when given alone or in combination with SKF38393."( Why does clozapine stimulate the motor activity of reserpine-pretreated rats when combined with a dopamine D1 receptor agonist?
Bengtsson, A; Jackson, DM; Malmberg, A; Mohell, N, 1995
)
0.29

Dosage Studied

ExcerptRelevanceReference
" Dose-response and time-response experiments were first performed to determine optimal conditions for measuring turnover in the quail brain."( Effects of alpha-methyl-para-tyrosine on monoamine levels in the Japanese quail: sex differences and testosterone effects.
Balthazart, J; Foidart, A; Hendrick, JC; Sante, P, 1992
)
0.28
" Dose-response studies of the effect of baclofen on prolactin (PRL) secretion were performed in stressed male rats."( Further evidence for the inhibitory action of baclofen on a prolactin-releasing factor.
Libertun, C; Lux-Lantos, V; Rey, E; Somoza, G, 1991
)
0.28
" The dose-response curve for APO-induced yawning was not changed by alpha MPT (200 mg/kg), while the suppression of exploration induced by APO, but not by pergolide, was enhanced by pretreatment with alpha MPT."( Yawning and suppression of exploration induced by dopamine agonists: no relation to extracellular striatal levels of dopamine.
Ståhle, L; Ungerstedt, U, 1990
)
0.28
" The dose-response curve for amphetamine was shifted downward and to the right by reserpine but was flattened by AMPT."( Depletion of catecholamines in the brain of rats differentially affects stimulation of locomotor activity by caffeine, D-amphetamine, and methylphenidate.
Finn, IB; Holtzman, SG; Iuvone, PM, 1990
)
0.28
" Dose-response curves for the effects of PPA and amphetamine (administered IP, 15 min presession) were then determined (ED50 = 35."( Evaluation of the pharmacological similarities between phenylpropanolamine and amphetamine: effects on schedule-controlled behavior.
Jarvis, MF; Wagner, GC, 1990
)
0.28
" Dose-response curves for methoxamine and vasopressin were not significantly different between groups."( Does enhanced sympathetic tone contribute to angiotensin II hypertension in rats?
Chow, KY; Kline, RL; Mercer, PF, 1990
)
0.28
"0 micrograms) inhibited the cocaine-induced hyperactivity in an U-shaped dose-response manner."( Oxytocin attenuates the cocaine-induced exploratory hyperactivity in mice.
Kovács, GL; Sarnyai, Z; Szabó, G; Telegdy, G,
)
0.13
" of clonidine, UK-14,304 and B-HT 933 respectively, and the log dose-response curves for all 3 agonists were bell-shaped."( The thermogenic actions of alpha 2-adrenoceptor agonists in reserpinized mice are mediated via a central postsynaptic alpha 2-adrenoceptor mechanism.
Bill, DJ; Hughes, IE; Stephens, RJ, 1989
)
0.28
" Yohimbine caused about a 30 fold shift to the right in the dose-response curve whereas idazoxan almost completely abolished the mydriatic response to (+)-Amp."( Mechanism of dexamphetamine-induced mydriasis in the anaesthetized rat.
Hey, JA; Ito, T; Koss, MC, 1989
)
0.28
" Its dose-response curve was bell-shaped with maximal effects at a dose of 100 micrograms/kg."( Occurrence of yawning and decrease of prolactin levels via stimulation of dopamine D2-receptors after administration of SND 919 in rats.
Domae, M; Furukawa, T; Matsumoto, S; Nagashima, M; Shirakawa, K; Yamada, K, 1989
)
0.28
" At 24 h post reserpine the dose-response curve of B-HT 920 (0."( Locomotor behaviour of selective dopamine agonists in mice: is endogenous dopamine the only catecholamine involved?
Pichler, L; Pifl, C, 1989
)
0.28
" These differences may be explained only partially by an increased susceptibility of the LS mice to the hypothermia and toxic effects caused by AMPT administration, as they persist with non-toxic AMPT dosage regimens and under conditions where the degree of hypothermia is comparable in both lines of mice."( Alpha-methyl-para-tyrosine effects in mice selectively bred for differences in sensitivity to ethanol.
Clay, KL; French, TA; Murphy, RC; Weiner, N, 1985
)
0.27
" Results of assays of norepinephrine and dopamine levels in MBH after the various treatments suggest that, at the dosage used, U-14,624 has a greater effect on norepinephrine and dopamine levels that the other dopamine-beta-hydroxylase inhibitors."( Some catecholamine inhibitors do not cause accumulation of nuclear estrogen receptors in rat hypothalamus and anterior pituitary gland.
Blaustein, JD; Brown, TJ; McElroy, JF, 1986
)
0.27
" The dose-response curve of detomidine was shifted to the right in a parallel manner by the selective alpha 2-antagonist idazoxan."( Effect of detomidine on the release and turnover of noradrenaline in rat brain.
Kaisila, M; MacDonald, E; Virtanen, R, 1986
)
0.27
" The dose-response relationship of LVP was non-linear."( Facilitatory effects of monoamine synthesis inhibitors on lysine-vasopressin induced changes in the exploratory behaviour pattern of male rats.
Höglund, AU; Meyerson, BJ, 1984
)
0.27
" The dose-response relationship shifted to the left following REMs deprivation (ED50 values in the group-housed, isolated, and REMs-deprived mice were 250, 200, and 27 micrograms/kg, respectively)."( Monoamine depletion attenuates the REM sleep deprivation-induced increase in clonidine response in the forced swimming test.
Asakura, W; Matsumoto, K; Ohta, H; Watanabe, H, 1994
)
0.29
" A muscarinic agonist, carbachol, produced a dose-related rightward shift of the dose-response curve to IMI."( Suppression of the rat micturition reflex by imipramine.
Kim, CY; Sohn, UD, 1997
)
0.3
" Overall, the dose-response and time-of-recovery relationships for altered NET expression matched those for production of antidepressant-like effects on behavior."( Norepinephrine transporter regulation mediates the long-term behavioral effects of the antidepressant desipramine.
Baros, AM; Bondi, CO; Lapiz, MD; Morilak, DA; O'Donnell, JM; Zhang, HT; Zhao, Z, 2008
)
0.35
"Repeated dosing with alpha-methyl-p-tyrosine (AMPT) at doses that significantly (-75%) depleted brain tissue dopamine levels resulted in increased (+36%) in vivo [(11)C]DTBZ binding to VMAT2 in the striatum."( In vivo [11C]dihydrotetrabenazine binding in rat striatum: sensitivity to dopamine concentrations.
Butch, ER; Desmond, T; Frey, KA; Harris, PE; Kilbourn, MR; Sherman, P, 2010
)
0.36
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Protein Targets (10)

Potency Measurements

ProteinTaxonomyMeasurementAverage (µ)Min (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Chain A, ATP-DEPENDENT DNA HELICASE Q1Homo sapiens (human)Potency11.22020.125919.1169125.8920AID2353
Chain A, CruzipainTrypanosoma cruziPotency0.12590.002014.677939.8107AID1476
dopamine D1 receptorHomo sapiens (human)Potency0.00920.00521.30228.1995AID624455
thioredoxin reductaseRattus norvegicus (Norway rat)Potency37.68580.100020.879379.4328AID488773; AID588453
regulator of G-protein signaling 4Homo sapiens (human)Potency0.29910.531815.435837.6858AID504845
arylsulfatase AHomo sapiens (human)Potency4.25621.069113.955137.9330AID720538
euchromatic histone-lysine N-methyltransferase 2Homo sapiens (human)Potency3.76860.035520.977089.1251AID504332
thyroid hormone receptor beta isoform aHomo sapiens (human)Potency0.00050.010039.53711,122.0200AID1479
peptidyl-prolyl cis-trans isomerase NIMA-interacting 1Homo sapiens (human)Potency37.93300.425612.059128.1838AID504536
neuropeptide S receptor isoform AHomo sapiens (human)Potency25.11890.015812.3113615.5000AID1461
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Bioassays (21)

Assay IDTitleYearJournalArticle
AID1347059CD47-SIRPalpha protein protein interaction - Alpha assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347405qHTS to identify inhibitors of the type 1 interferon - major histocompatibility complex class I in skeletal muscle: primary screen against the NCATS LOPAC collection2020ACS chemical biology, 07-17, Volume: 15, Issue:7
High-Throughput Screening to Identify Inhibitors of the Type I Interferon-Major Histocompatibility Complex Class I Pathway in Skeletal Muscle.
AID1508630Primary qHTS for small molecule stabilizers of the endoplasmic reticulum resident proteome: Secreted ER Calcium Modulated Protein (SERCaMP) assay2021Cell reports, 04-27, Volume: 35, Issue:4
A target-agnostic screen identifies approved drugs to stabilize the endoplasmic reticulum-resident proteome.
AID1347086qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lymphocytic Choriomeningitis Arenaviruses (LCMV): LCMV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347082qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: LASV Primary Screen - GLuc reporter signal2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID1347045Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot counterscreen GloSensor control cell line2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347057CD47-SIRPalpha protein protein interaction - LANCE assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1347410qHTS for inhibitors of adenylyl cyclases using a fission yeast platform: a pilot screen against the NCATS LOPAC library2019Cellular signalling, 08, Volume: 60A fission yeast platform for heterologous expression of mammalian adenylyl cyclases and high throughput screening.
AID1347050Natriuretic polypeptide receptor (hNpr2) antagonism - Pilot subtype selectivity assay2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347049Natriuretic polypeptide receptor (hNpr1) antagonism - Pilot screen2019Science translational medicine, 07-10, Volume: 11, Issue:500
Inhibition of natriuretic peptide receptor 1 reduces itch in mice.
AID1347083qHTS for Inhibitors of the Functional Ribonucleoprotein Complex (vRNP) of Lassa (LASV) Arenavirus: Viability assay - alamar blue signal for LASV Primary Screen2020Antiviral research, 01, Volume: 173A cell-based, infectious-free, platform to identify inhibitors of lassa virus ribonucleoprotein (vRNP) activity.
AID588378qHTS for Inhibitors of ATXN expression: Validation
AID504836Inducers of the Endoplasmic Reticulum Stress Response (ERSR) in human glioma: Validation2002The Journal of biological chemistry, Apr-19, Volume: 277, Issue:16
Sustained ER Ca2+ depletion suppresses protein synthesis and induces activation-enhanced cell death in mast cells.
AID504812Inverse Agonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID1347151Optimization of GU AMC qHTS for Zika virus inhibitors: Unlinked NS2B-NS3 protease assay2020Proceedings of the National Academy of Sciences of the United States of America, 12-08, Volume: 117, Issue:49
Therapeutic candidates for the Zika virus identified by a high-throughput screen for Zika protease inhibitors.
AID504810Antagonists of the Thyroid Stimulating Hormone Receptor: HTS campaign2010Endocrinology, Jul, Volume: 151, Issue:7
A small molecule inverse agonist for the human thyroid-stimulating hormone receptor.
AID588349qHTS for Inhibitors of ATXN expression: Validation of Cytotoxic Assay
AID1347058CD47-SIRPalpha protein protein interaction - HTRF assay qHTS validation2019PloS one, , Volume: 14, Issue:7
Quantitative high-throughput screening assays for the discovery and development of SIRPα-CD47 interaction inhibitors.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).2014Journal of biomolecular screening, Jul, Volume: 19, Issue:6
A High-Throughput Assay to Identify Inhibitors of the Apicoplast DNA Polymerase from Plasmodium falciparum.
AID1794808Fluorescence-based screening to identify small molecule inhibitors of Plasmodium falciparum apicoplast DNA polymerase (Pf-apPOL).
AID1159607Screen for inhibitors of RMI FANCM (MM2) intereaction2016Journal of biomolecular screening, Jul, Volume: 21, Issue:6
A High-Throughput Screening Strategy to Identify Protein-Protein Interaction Inhibitors That Block the Fanconi Anemia DNA Repair Pathway.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (1,114)

TimeframeStudies, This Drug (%)All Drugs %
pre-1990464 (41.65)18.7374
1990's369 (33.12)18.2507
2000's168 (15.08)29.6817
2010's94 (8.44)24.3611
2020's19 (1.71)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Market Indicators

Research Demand Index: 7.17

According to the monthly volume, diversity, and competition of internet searches for this compound, as well the volume and growth of publications, there is estimated to be weak demand-to-supply ratio for research on this compound.

MetricThis Compound (vs All)
Research Demand Index7.17 (24.57)
Research Supply Index7.10 (2.92)
Research Growth Index4.27 (4.65)
Search Engine Demand Index0.00 (26.88)
Search Engine Supply Index0.00 (0.95)

This Compound (7.17)

All Compounds (24.57)

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials45 (3.86%)5.53%
Reviews20 (1.72%)6.00%
Case Studies32 (2.75%)4.05%
Observational0 (0.00%)0.25%
Other1,068 (91.67%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]