Compounds > 1-phenethylamine, (r)-isomer
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1-phenethylamine, (r)-isomer

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Description

## 1-Phenethylamine, (R)-Isomer: A Key for Research

**1-Phenethylamine** is a simple organic compound with the formula C8H11N. It is the parent molecule for a variety of psychoactive and pharmaceutical compounds, including amphetamine and methamphetamine.

**The (R)-isomer** refers to the **stereoisomer** of 1-phenethylamine, where the amine group (-NH2) is specifically located on the *right* side of the molecule. This specific arrangement of atoms influences its interaction with receptors and enzymes, making it distinct from its (S)-isomer.

**Why is it important for research?**

The (R)-isomer of 1-phenethylamine plays a crucial role in research for several reasons:

1. **Understanding Receptor Interactions:** It acts as a **tracer molecule** in studies investigating the **binding and activation of various receptors** in the brain, including:
* **Trace amine-associated receptor 1 (TAAR1)**: This receptor is involved in regulating dopamine and serotonin release, with potential implications for mood, attention, and addiction.
* **α1-adrenergic receptor:** This receptor is important in the sympathetic nervous system, regulating blood pressure, heart rate, and other bodily functions.
2. **Pharmacological Studies:** The (R)-isomer is used as a **starting point for developing new drugs** by:
* Investigating its **pharmacological properties** and potential therapeutic applications.
* Synthesizing **analogs** with modified structures to enhance specific properties and improve drug efficacy.
3. **Neurochemical Research:** It helps researchers understand the **role of trace amines** in the brain and their relationship to:
* **Neurotransmission** and the modulation of neurotransmitter activity.
* **Neurodegenerative diseases** like Parkinson's and Alzheimer's.
* **Mental health conditions** like depression, anxiety, and schizophrenia.

**Key points to remember:**

* The (R)-isomer of 1-phenethylamine is crucial for understanding the complex interactions of trace amines with the brain.
* Its research applications extend beyond the neurochemical domain and touch upon pharmacological and medical fields.
* Understanding the specific properties of this isomer can pave the way for developing novel therapeutic interventions for a wide range of conditions.

**Disclaimer:** This information is intended for informational purposes only and should not be taken as medical advice. Consult with a qualified healthcare professional before making any decisions about your health or treatment.

(1R)-1-phenylethanamine : The (R)-enantiomer of 1-phenylethanamine. [Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Cross-References

ID SourceID
PubMed CID643189
CHEMBL ID19969
CHEBI ID35322
SCHEMBL ID42393
SCHEMBL ID4165369
MeSH IDM0319776

Synonyms (99)

Synonym
benzenemethanamine, .alpha.-methyl-, (.alpha.r)-
d-alpha-methylbenzylamine
(alphar)-alpha-methylbenzenemethanamine
CHEBI:35322 ,
3886-69-9
(r)-alpha-methylbenzenemethanamine
(1r)-1-phenylethanamine
(r)-(+)-alpha-methylbenzylamine, 98%
(r)-(+)-alpha-methylbenzylamine
(r)1-phenyl-ethylamine
CHEMBL19969 ,
(r)-(+)-1-phenylethylamine
P0794
(r)-1-phenylethylamine
bdbm50028628
A6546
(r)-1-phenylethanamine
AKOS005256786
(+)-1-phenethylamine
EN300-67366
(r)-(+)-1-methylbenzylamine
(1r)-1-phenylethan-1-amine
r-(+)-alpha-methylbenzylamine
v022zk8gz5 ,
1-phenethylamine, (+)-
unii-v022zk8gz5
ec 223-423-4
einecs 223-423-4
benzenemethanamine, alpha-methyl-, (alphar)-
AM20060613
d-(+)-2-amino-1-butanol
qsc ,
d-.alpha.-methylbenzylamine
(r)-(+)-1-phenethylamine
r-(+)-methylbenzylamine
(r)-(+)-1-phenylethanamine
d-1-phenylethylamine
.alpha.-methylbenzylamine (+)-form [mi]
d-.alpha.-phenethylamine
SCHEMBL42393
(r)alpha-methylbenzylamine
(r)-(1-phenylethyl)amine
(+)-(r)-alpha-methylbenzenemethanamine
(r)-(+)-alpha-methyl benzylamine
1(r)-phenyl ethyl amine
RQEUFEKYXDPUSK-SSDOTTSWSA-N
(+)-(r)-alpha-methylbenzylamine
(r)-alpha-methylbenzylamine
(r)-a-methylbenzylamine
(r)-1-phenylethylarnine
(r)-1-(phenyl)-ethylamine
[r]-(+)-1-phenylethylamine
(r)-(-)-alpha-methylbenzylamine
(r)-1-phenylethan-1-amine
(r)-1-phenyl ethylamine
(r)-alpha-methylbenzylarnine
(1r)-1-phenyl-ethylamine
(1 r)-1-phenylethanamine
[(1r)-1-phenylethyl]amine
(r)-1-phenyl-ethylamine
(r)-(+)-alpha-methyl-benzylamine
(1r)-(+)-1-phenylethylamine
(r)-(+)-a-methylbenzylamine
r-(+)-alpha methylbenzylamine
(r)-alpha-methyl benzylamine
(r)-(+)-alpha-methylbenzyl amine
[r]-1-phenylethylamine
(1r)-1-phenylethylamine
(r)-1-phenyl-ethyl-amine
(r)-(-)-1-phenylethylamine
(+)-(r)-alpha-methyl-benzenemethanamine
(1r)-1-phenyl-1-ethanamine
SCHEMBL4165369
Q-200619
alpha-formylmandeloyl chloride
Q-200923
r(+)-|a-phenylethylamine
(r)-(+)-|a-methylbenzylamine
mfcd00064405
r(+)-1-phenylethylamine
F8889-8738
(r)-(+)-alpha-methylbenzylamine, for chiral derivatization, >=99.0%
(r)-(+)-alpha-methylbenzylamine, chipros(r), produced by basf, >=99.0%
(r)-(+)-alpha-methylbenzylamine, purum, >=98.0% (sum of enantiomers, gc)
CS-W008645
AC-8773
(r)-(+)-alpha-methylbenzylamine, >=99%, chiraselect(tm)
D77692
(+)-alpha-phenylethylamine
levetiracetam impurity e, european pharmacopoeia (ep) reference standard
(r)-(+)-?-methylbenzylamine
DTXSID80930735
Q27116453
r(+)alpha-methylbenzylamine
(r)-phenylethylamine
(r)-2-phenylethylamine
(r)-(+)- alpha -methylbenzylamine
(alphar)-alpha-methyl-benzenemethanamine (+)-alpha-phenethylamine (r)-1-amino-1-phenylethane
Z1079183182
[information is derived through text-mining from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Drug Classes (1)

ClassDescription
1-phenylethylamineA phenylethylamine that is ethylamine substituted by a phenyl group at position 1.
[compound class information is derived from Chemical Entities of Biological Interest (ChEBI), Hastings J, Owen G, Dekker A, Ennis M, Kale N, Muthukrishnan V, Turner S, Swainston N, Mendes P, Steinbeck C. (2016). ChEBI in 2016: Improved services and an expanding collection of metabolites. Nucleic Acids Res]

Protein Targets (6)

Inhibition Measurements

ProteinTaxonomyMeasurementAverageMin (ref.)Avg (ref.)Max (ref.)Bioassay(s)
Phenylethanolamine N-methyltransferaseBos taurus (cattle)Ki154,149,991.50000.00312.329310.0000AID145544; AID155306; AID156064
Phenylethanolamine N-methyltransferaseHomo sapiens (human)Ki4,800.00000.00161.35296.9000AID155320
Alpha-2B adrenergic receptorRattus norvegicus (Norway rat)Ki3,467,369,984.00000.00000.929610.0000AID35395
Alpha-2C adrenergic receptorRattus norvegicus (Norway rat)Ki3,467,369,984.00000.00000.970810.0000AID35395
Alpha-2A adrenergic receptorRattus norvegicus (Norway rat)Ki3,467,369,984.00000.00000.937510.0000AID35395
Amine oxidase [flavin-containing] BBos taurus (cattle)Ki190.00000.05401.83906.0000AID125204
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Processvia Protein(s)Taxonomy
methylationPhenylethanolamine N-methyltransferaseBos taurus (cattle)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseBos taurus (cattle)
methylationPhenylethanolamine N-methyltransferaseHomo sapiens (human)
epinephrine biosynthetic processPhenylethanolamine N-methyltransferaseHomo sapiens (human)
catecholamine biosynthetic processPhenylethanolamine N-methyltransferaseHomo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Processvia Protein(s)Taxonomy
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseBos taurus (cattle)
phenylethanolamine N-methyltransferase activityPhenylethanolamine N-methyltransferaseHomo sapiens (human)
protein bindingPhenylethanolamine N-methyltransferaseHomo sapiens (human)
primary amine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
aliphatic amine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
monoamine oxidase activityAmine oxidase [flavin-containing] BBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Processvia Protein(s)Taxonomy
cytosolPhenylethanolamine N-methyltransferaseHomo sapiens (human)
cytosolPhenylethanolamine N-methyltransferaseHomo sapiens (human)
mitochondrionAmine oxidase [flavin-containing] BBos taurus (cattle)
mitochondrial outer membraneAmine oxidase [flavin-containing] BBos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay IDTitleYearJournalArticle
AID125207Competitive inhibition of Bovine liver Monoamine Oxidase B at 30 degree C (pH= 9.0)1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Stereoisomers of allenic amines as inactivators of monoamine oxidase type B. Stereochemical probes of the active site.
AID155337Ki ratio of human versus bovine phenylethanolamine N-methyl-transferase2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID155320Inhibitory constant against human phenylethanolamine N-methyl-transferase over-expressed in Escherichia coli2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID145544Inhibitory activity against bovine adrenal norepinephrine N-methyl-transferase was determined1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Probes of the active site of norepinephrine N-methyltransferase: effect of hydrophobic and hydrophilic interactions on side-chain binding of amphetamine and alpha-methylbenzylamine.
AID35395Inhibition of [3H]clonidine binding to the rat alpha-2-adrenoceptor1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the alpha2-adrenoceptor: the development of new, highly selective inhibitors of PNMT.
AID145543Inhibitory activity against Norepinephrine N-methyl-transferase of bovine adrenal glands1982Journal of medicinal chemistry, Oct, Volume: 25, Issue:10
Importance of the aromatic ring in adrenergic amines. 7. Comparison of the stereoselectivity of norepinephrine N-methyltransferase for aromatic vs. nonaromatic substrates and inhibitors.
AID353104Ratio of Ki for rat brain NMDA receptor in presence of 100 uM spermine to Ki for rat brain NMDA receptor in absence of spermine2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID156064Inhibitory activity against bovine adrenal phenylethanolamine N-methyl-transferase (PNMT)1999Bioorganic & medicinal chemistry letters, Feb-08, Volume: 9, Issue:3
Comparative molecular field analysis (CoMFA) models of phenylethanolamine N-methyltransferase (PNMT) and the alpha2-adrenoceptor: the development of new, highly selective inhibitors of PNMT.
AID155306Inhibitory constant against bovine phenylethanolamine N-methyl-transferase2001Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12
Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID353103Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane2009Bioorganic & medicinal chemistry, May-01, Volume: 17, Issue:9
NMDA receptor affinities of 1,2-diphenylethylamine and 1-(1,2-diphenylethyl)piperidine enantiomers and of related compounds.
AID125204In vitro inhibition of bovine monoamine oxidase B.1988Journal of medicinal chemistry, Aug, Volume: 31, Issue:8
Stereoisomers of allenic amines as inactivators of monoamine oxidase type B. Stereochemical probes of the active site.
[information is prepared from bioassay data collected from National Library of Medicine (NLM), extracted Dec-2023]

Research

Studies (6)

TimeframeStudies, This Drug (%)All Drugs %
pre-19903 (50.00)18.7374
1990's1 (16.67)18.2507
2000's2 (33.33)29.6817
2010's0 (0.00)24.3611
2020's0 (0.00)2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication TypeThis drug (%)All Drugs (%)
Trials0 (0.00%)5.53%
Reviews0 (0.00%)6.00%
Case Studies0 (0.00%)4.05%
Observational0 (0.00%)0.25%
Other6 (100.00%)84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]
SubstanceRelationship StrengthStudiesTrialsClassesRoles
phenethylamine
phenethylamine: RN given refers to parent cpd; structure in Merck Index, 9th ed, #7016. 2-phenylethylamine : A phenylethylamine having the phenyl substituent at the 2-position.		2.3920alkaloid;
aralkylamine;
phenylethylamine		Escherichia coli metabolite;
human metabolite;
mouse metabolite
2,3-dichloro-alpha-methylbenzylamine
2,3-dichloro-alpha-methylbenzylamine: inhibitor of phenethanolamine N-methyltransferase; RN given refers to parent cpd without isomeric designation; structure		210
2-cyclooctyl-2-hydroxyethylamine
2-cyclooctyl-2-hydroxyethylamine: RN given refers to parent cpd		2.3820
amphetamine
Amphetamine: A powerful central nervous system stimulant and sympathomimetic. Amphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulation of release of monamines, and inhibiting monoamine oxidase. Amphetamine is also a drug of abuse and a psychotomimetic. The l- and the d,l-forms are included here. The l-form has less central nervous system activity but stronger cardiovascular effects. The d-form is DEXTROAMPHETAMINE.. 1-phenylpropan-2-amine : A primary amine that is isopropylamine in which a hydrogen attached to one of the methyl groups has been replaced by a phenyl group.. amphetamine : A racemate comprising equimolar amounts of (R)-amphetamine (also known as levamphetamine or levoamphetamine) and (S)-amphetamine (also known as dexamfetamine or dextroamphetamine.		2.3620primary amine
sk&f 29661
1,2,3,4-tetrahydroisoquinoline-7-sulfonamide: structure		2.4120
dextroamphetamine
Dextroamphetamine: The d-form of AMPHETAMINE. It is a central nervous system stimulant and a sympathomimetic. It has also been used in the treatment of narcolepsy and of attention deficit disorders and hyperactivity in children. Dextroamphetamine has multiple mechanisms of action including blocking uptake of adrenergics and dopamine, stimulating release of monamines, and inhibiting monoamine oxidase. It is also a drug of abuse and a psychotomimetic.. (S)-amphetamine : A 1-phenylpropan-2-amine that has S configuration.		2.89401-phenylpropan-2-amineadrenergic agent;
adrenergic uptake inhibitor;
dopamine uptake inhibitor;
dopaminergic agent;
neurotoxin;
sympathomimetic agent
phencyclidine
Phencyclidine: A hallucinogen formerly used as a veterinary anesthetic, and briefly as a general anesthetic for humans. Phencyclidine is similar to KETAMINE in structure and in many of its effects. Like ketamine, it can produce a dissociative state. It exerts its pharmacological action through inhibition of NMDA receptors (RECEPTORS, N-METHYL-D-ASPARTATE). As a drug of abuse, it is known as PCP and Angel Dust.. phencyclidine : A member of the class of piperidines that is piperidine in which the nitrogen is substituted with a 1-phenylcyclohexyl group. Formerly used as an anaesthetic agent, it exhibits both hallucinogenic and neurotoxic effects.		2.0510benzenes;
piperidines		anaesthetic;
neurotoxin;
NMDA receptor antagonist;
psychotropic drug
benzhydrylamine
[no description available]		2.0510
1,2,3,4-tetrahydroisoquinoline
1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified		2.4120isoquinolines
1-phenethylamine
1-phenethylamine: RN given refers to cpd without isomeric designation. 1-phenylethylamine : A phenylethylamine that is ethylamine substituted by a phenyl group at position 1.		2.6630phenylethylaminehuman metabolite
benzylamine
aminotoluene : Any member of the class of toluenes carrying one or more amino groups.		2.4220aralkylamine;
primary amine		allergen;
EC 3.5.5.1 (nitrilase) inhibitor;
plant metabolite
methamphetamine
Methamphetamine: A central nervous system stimulant and sympathomimetic with actions and uses similar to DEXTROAMPHETAMINE. The smokable form is a drug of abuse and is referred to as crank, crystal, crystal meth, ice, and speed.. methamphetamine : A member of the class of amphetamines in which the amino group of (S)-amphetamine carries a methyl substituent.		1.9710amphetamines;
secondary amine		central nervous system stimulant;
environmental contaminant;
neurotoxin;
psychotropic drug;
xenobiotic
2-methyl-1,2,3,4-tetrahydroisoquinoline
[no description available]		210
tranylcypromine
Tranylcypromine: A propylamine formed from the cyclization of the side chain of amphetamine. This monoamine oxidase inhibitor is effective in the treatment of major depression, dysthymic disorder, and atypical depression. It also is useful in panic and phobic disorders. (From AMA Drug Evaluations Annual, 1994, p311). tranylcypromine : A racemate comprising equal amounts of (1R,2S)- and (1S,2R)-2-phenylcyclopropan-1-amine. An irreversible monoamine oxidase inhibitor that is used as an antidepressant (INN tranylcypromine).. (1R,2S)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1R,2S)-enantiomer of tranylcypromine.		2.05102-phenylcyclopropan-1-amine
(1S,2R)-tranylcypromine
(1S,2R)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1S,2R)-enantiomer of tranylcypromine.		2.05102-phenylcyclopropan-1-amine
exp561
EXP561: inhibitor of 5-HT uptake; RN given refers to parent cpd		210
l-amphetamine
(R)-amphetamine : A 1-phenylpropan-2-amine that has R configuration.		2.67301-phenylpropan-2-amine
norsalsolinol
norsalsolinol: rigid dopamine analog; RN given refers to parent cpd; structure. norsalsolinol : An isoquinolinol that is 1,2,3,4-tetrahydroisoquinoline substituted by hydroxy groups at positions 6 and 7. It is present in the dopamine-rich areas of the human brain, including the substantia nigra.		210isoquinolinolanimal metabolite;
apoptosis inducer;
human metabolite;
marine metabolite
1-phenethylamine, (s)-isomer
(1S)-1-phenylethanamine : The (S)-enantiomer of 1-phenylethanamine.		3.23601-phenylethylamine
1,3-diphenyl-2-aminopropane
1,3-diphenyl-2-aminopropane: structure given in the first source		1.9610
2-aminobenzonorbornene
2-aminobenzonorbornene: RN given refers to (endo, 1alpha,2beta,4alpha)-isomer		210
ly 134046
LY 134046: RN given refers to parent cpd; structure in first source		2.4120
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline
7,8-dichloro-1,2,3,4-tetrahydroisoquinoline: potent reversible inhibitor of phenylethanolamine N-methyltransferase; structure. 7,8-dichloro-1,2,3,4-tetrahydroisoquinoline : A 1,2,3,4-tetrahydroisoquinoline hacing chloro substituents at the 7- and 8-positions.		2.4120isoquinolines;
organochlorine compound
dizocilpine
[no description available]		2.0510secondary amino compound;
tetracyclic antidepressant		anaesthetic;
anticonvulsant;
neuroprotective agent;
nicotinic antagonist;
NMDA receptor antagonist
esketamine
esketamine : The S- (more active) enantiomer of ketamine.		2.0510ketamineanalgesic;
intravenous anaesthetic;
NMDA receptor antagonist
phenylalaninol
phenylalaninol: inhibits intestinal absorption of phenylalanine; RN given refers to cpd with unspecified stereochemistry. L-phenylalaninol : An amino alcohol resulting from the formal reduction of the carboxy group of L-phenylalanine to the corresponding alcohol.		1.9610amino alcohol;
amphetamines;
primary alcohol;
primary amino compound
(R)-ketamine
(R)-ketamine : The R- (less active) enantiomer of ketamine.		2.0510ketamineanalgesic;
intravenous anaesthetic;
NMDA receptor antagonist
phenylalanine methyl ester
phenylalanine methyl ester: RN given refers to (L)-isomer. methyl L-phenylalaninate : An alpha-amino acid ester that is the methyl ester of L-phenylalanine.		2.0510alpha-amino acid ester;
L-phenylalanine derivative
meso-1,2-diphenylethylenediamine, (r-(r*,s*))-isomer
diphenylethylenediamine: structure in first source		2.0510
dextromethorphan
Dextromethorphan: Methyl analog of DEXTRORPHAN that shows high affinity binding to several regions of the brain, including the medullary cough center. This compound is an NMDA receptor antagonist (RECEPTORS, N-METHYL-D-ASPARTATE) and acts as a non-competitive channel blocker. It is one of the widely used ANTITUSSIVES, and is also used to study the involvement of glutamate receptors in neurotoxicity.. dextromethorphan : A 6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene in which the sterocenters at positions 4a, 10 and 10a have S-configuration. It is a prodrug of dextrorphan and used as an antitussive drug for suppressing cough.		2.05106-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthreneantitussive;
environmental contaminant;
neurotoxin;
NMDA receptor antagonist;
oneirogen;
prodrug;
xenobiotic
fpl 15896ar
[no description available]		2.0510
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline: structure in first source		210
ConditionIndicatedRelationship StrengthStudiesTrials