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 Source	ID
PubMed CID	643189
CHEMBL ID	19969
CHEBI ID	35322
SCHEMBL ID	42393
SCHEMBL ID	4165369
MeSH ID	M0319776

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)

Class	Description
1-phenylethylamine	A 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

Protein	Taxonomy	Measurement	Average	Min (ref.)	Avg (ref.)	Max (ref.)	Bioassay(s)
Phenylethanolamine N-methyltransferase	Bos taurus (cattle)	Ki	154,149,991.5000	0.0031	2.3293	10.0000	AID145544; AID155306; AID156064
Phenylethanolamine N-methyltransferase	Homo sapiens (human)	Ki	4,800.0000	0.0016	1.3529	6.9000	AID155320
Alpha-2B adrenergic receptor	Rattus norvegicus (Norway rat)	Ki	3,467,369,984.0000	0.0000	0.9296	10.0000	AID35395
Alpha-2C adrenergic receptor	Rattus norvegicus (Norway rat)	Ki	3,467,369,984.0000	0.0000	0.9708	10.0000	AID35395
Alpha-2A adrenergic receptor	Rattus norvegicus (Norway rat)	Ki	3,467,369,984.0000	0.0000	0.9375	10.0000	AID35395
Amine oxidase [flavin-containing] B	Bos taurus (cattle)	Ki	190.0000	0.0540	1.8390	6.0000	AID125204
[prepared from compound, protein, and bioassay information from National Library of Medicine (NLM), extracted Dec-2023]

Biological Processes (3)

Process	via Protein(s)	Taxonomy
methylation	Phenylethanolamine N-methyltransferase	Bos taurus (cattle)
epinephrine biosynthetic process	Phenylethanolamine N-methyltransferase	Bos taurus (cattle)
methylation	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
epinephrine biosynthetic process	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
catecholamine biosynthetic process	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
[Information is prepared from geneontology information from the June-17-2024 release]

Molecular Functions (5)

Process	via Protein(s)	Taxonomy
phenylethanolamine N-methyltransferase activity	Phenylethanolamine N-methyltransferase	Bos taurus (cattle)
phenylethanolamine N-methyltransferase activity	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
protein binding	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
primary amine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
aliphatic amine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
monoamine oxidase activity	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Ceullar Components (3)

Process	via Protein(s)	Taxonomy
cytosol	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
cytosol	Phenylethanolamine N-methyltransferase	Homo sapiens (human)
mitochondrion	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
mitochondrial outer membrane	Amine oxidase [flavin-containing] B	Bos taurus (cattle)
[Information is prepared from geneontology information from the June-17-2024 release]

Bioassays (11)

Assay ID	Title	Year	Journal	Article
AID125207	Competitive inhibition of Bovine liver Monoamine Oxidase B at 30 degree C (pH= 9.0)	1988	Journal 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.
AID155337	Ki ratio of human versus bovine phenylethanolamine N-methyl-transferase	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID155320	Inhibitory constant against human phenylethanolamine N-methyl-transferase over-expressed in Escherichia coli	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID145544	Inhibitory activity against bovine adrenal norepinephrine N-methyl-transferase was determined	1982	Journal 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.
AID35395	Inhibition of [3H]clonidine binding to the rat alpha-2-adrenoceptor	1999	Bioorganic & 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.
AID145543	Inhibitory activity against Norepinephrine N-methyl-transferase of bovine adrenal glands	1982	Journal 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.
AID353104	Ratio of Ki for rat brain NMDA receptor in presence of 100 uM spermine to Ki for rat brain NMDA receptor in absence of spermine	2009	Bioorganic & 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.
AID156064	Inhibitory activity against bovine adrenal phenylethanolamine N-methyl-transferase (PNMT)	1999	Bioorganic & 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.
AID155306	Inhibitory constant against bovine phenylethanolamine N-methyl-transferase	2001	Bioorganic & medicinal chemistry letters, Jun-18, Volume: 11, Issue:12	Phenylethanolamine N-methyltransferase kinetics: bovine versus recombinant human enzyme.
AID353103	Displacement of [3H]MK801 from NMDA receptor in rat brain neuronal membrane	2009	Bioorganic & 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.
AID125204	In vitro inhibition of bovine monoamine oxidase B.	1988	Journal 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)

Timeframe	Studies, This Drug (%)	All Drugs %
pre-1990	3 (50.00)	18.7374
1990's	1 (16.67)	18.2507
2000's	2 (33.33)	29.6817
2010's	0 (0.00)	24.3611
2020's	0 (0.00)	2.80
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Study Types

Publication Type	This drug (%)	All Drugs (%)
Trials	0 (0.00%)	5.53%
Reviews	0 (0.00%)	6.00%
Case Studies	0 (0.00%)	4.05%
Observational	0 (0.00%)	0.25%
Other	6 (100.00%)	84.16%
[information is prepared from research data collected from National Library of Medicine (NLM), extracted Dec-2023]

Substance	Relationship Strength	Studies	Classes	Roles
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.	2.39	2	alkaloid; 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	2	1
2-cyclooctyl-2-hydroxyethylamine 2-cyclooctyl-2-hydroxyethylamine: RN given refers to parent cpd	2.38	2
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.	2.36	2	primary amine
sk&f 29661 1,2,3,4-tetrahydroisoquinoline-7-sulfonamide: structure	2.41	2
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.	2.89	4	1-phenylpropan-2-amine	adrenergic 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.	2.05	1	benzenes; piperidines	anaesthetic; neurotoxin; NMDA receptor antagonist; psychotropic drug
benzhydrylamine [no description available]	2.05	1
1,2,3,4-tetrahydroisoquinoline 1,2,3,4-tetrahydroisoquinoline: RN given refers to cpd with locants as specified	2.41	2	isoquinolines
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.	2.66	3	phenylethylamine	human metabolite
benzylamine aminotoluene : Any member of the class of toluenes carrying one or more amino groups.	2.42	2	aralkylamine; 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.	1.97	1	amphetamines; secondary amine	central nervous system stimulant; environmental contaminant; neurotoxin; psychotropic drug; xenobiotic
2-methyl-1,2,3,4-tetrahydroisoquinoline [no description available]	2	1
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.	2.05	1	2-phenylcyclopropan-1-amine
(1S,2R)-tranylcypromine (1S,2R)-tranylcypromine : A 2-phenylcyclopropan-1-amine that is the (1S,2R)-enantiomer of tranylcypromine.	2.05	1	2-phenylcyclopropan-1-amine
exp561 EXP561: inhibitor of 5-HT uptake; RN given refers to parent cpd	2	1
l-amphetamine (R)-amphetamine : A 1-phenylpropan-2-amine that has R configuration.	2.67	3	1-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.	2	1	isoquinolinol	animal metabolite; apoptosis inducer; human metabolite; marine metabolite
1-phenethylamine, (s)-isomer (1S)-1-phenylethanamine : The (S)-enantiomer of 1-phenylethanamine.	3.23	6	1-phenylethylamine
1,3-diphenyl-2-aminopropane 1,3-diphenyl-2-aminopropane: structure given in the first source	1.96	1
2-aminobenzonorbornene 2-aminobenzonorbornene: RN given refers to (endo, 1alpha,2beta,4alpha)-isomer	2	1
ly 134046 LY 134046: RN given refers to parent cpd; structure in first source	2.41	2
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.	2.41	2	isoquinolines; organochlorine compound
dizocilpine [no description available]	2.05	1	secondary amino compound; tetracyclic antidepressant	anaesthetic; anticonvulsant; neuroprotective agent; nicotinic antagonist; NMDA receptor antagonist
esketamine esketamine : The S- (more active) enantiomer of ketamine.	2.05	1	ketamine	analgesic; 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.	1.96	1	amino alcohol; amphetamines; primary alcohol; primary amino compound
(R)-ketamine (R)-ketamine : The R- (less active) enantiomer of ketamine.	2.05	1	ketamine	analgesic; 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.	2.05	1	alpha-amino acid ester; L-phenylalanine derivative
meso-1,2-diphenylethylenediamine, (r-(r,s))-isomer diphenylethylenediamine: structure in first source	2.05	1
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.	2.05	1	6-methoxy-11-methyl-1,3,4,9,10,10a-hexahydro-2H-10,4a-(epiminoethano)phenanthrene	antitussive; environmental contaminant; neurotoxin; NMDA receptor antagonist; oneirogen; prodrug; xenobiotic
fpl 15896ar [no description available]	2.05	1
3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline 3-trifluoromethyl-7-bromo-1,2,3,4-tetrahydroisoquinoline: structure in first source	2	1

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