Methylephedrine

Details

• Internal ID: fa3af354-5c3c-44ae-9afe-612809af4b69
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
• SMILES (Canonical): CC(C(C1=CC=CC=C1)O)N(C)C
• SMILES (Isomeric): C[C@@H]([C@@H](C1=CC=CC=C1)O)N(C)C
• InChI: InChI=1S/C11H17NO/c1-9(12(2)3)11(13)10-7-5-4-6-8-10/h4-9,11,13H,1-3H3/t9-,11-/m0/s1
• InChI Key: FMCGSUUBYTWNDP-ONGXEEELSA-N
• Popularity: 335 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₁H₁₇NO
• Molecular Weight: 179.26 g/mol
• Exact Mass: 179.131014166 g/mol
• Topological Polar Surface Area (TPSA): 23.50 Ų
• XlogP: 1.70
• Atomic LogP (AlogP): 1.67
• H-Bond Acceptor: 2
• H-Bond Donor: 1
• Rotatable Bonds: 3

Synonyms

• 552-79-4
• (1R,2S)-2-(dimethylamino)-1-phenylpropan-1-ol
• Tybraine
• dl-methylephedrine
• (-)-N-Methylephedrine
• Methylephedrine, (+/-)-
• Methylephedrine, DL-
• Methylephedrine [BAN]
• SHS9PGQ2LS
• (+/-)-Methylephedrine
• EINECS 209-022-7
• (1R,2S)-2-Dimethylamino-1-phenyl-1-propanol
• (+/-)-n-methylephedrine
• Methylephedrine [INN:BAN]
• UNII-60VH42A1KJ
• L-erythro-2-Dimethylamino-1-phenylpropanol
• 60VH42A1KJ
• DTXSID7045992
• methylephedrine HCl
• L-erythro-alpha-(1-Dimethylaminoethyl)benzylalkohol
• N-METHYL (-)EPHEDRINE
• NSC-760389
• Methylephedrine (BAN)
• (1R,2S)-2-(dimethylamino)-1-phenyl-1-propanol
• (1Rs,2Rs)-2-dimethylamino-1-phenylpropan-1-ol
• methylephedrine hydrochloride
• Benzenemethanol, alpha-((1S)-1-(dimethylamino)ethyl)-, (alphaR)-
• Methylephedrine ((1R,2S)-Methylephedrine)
• Erythro-alpha-[1-(dimethylamino)ethyl]benzyl alcohol
• L-Methylephedrine
• (1s,2s)-(+)-n-Methylephedrine
• NCGC00095782-01
• 1201-56-5
• (-)-methylephedrine
• Spectrum_000431
• UNII-SHS9PGQ2LS
• Spectrum2_001196
• Spectrum3_000671
• Spectrum4_000739
• Spectrum5_001055
• N-methylephedrine DL-form
• SCHEMBL99673
• BSPBio_002361
• KBioGR_001038
• KBioSS_000911
• N-METHYL(-)EPHEDRINE
• DivK1c_000283
• SPECTRUM2300220
• SPBio_001271
• N-METHYLEPHEDRINE [MI]
• CHEMBL445001
• DTXCID5025992
• METHYLEPHEDRINE [WHO-DD]
• (1r,2s)-(-)n-methylephedrine
• HMS500O05
• KBio1_000283
• KBio2_000911
• KBio2_003479
• KBio2_006047
• KBio3_001581
• CHEBI:113556
• FMCGSUUBYTWNDP-ONGXEEELSA-N
• NINDS_000283
• HMS3264G05
• Pharmakon1600-02300220
• N-methyl-(-)ephedrine-[1R,2S]
• EINECS 214-859-6
• Tox21_111521
• CCG-39547
• N-Methylephedrine; LC-tDDA; CE10
• NSC760389
• AKOS006281830
• DB11278
• N-METHYLEPHEDRINE DL-FORM [MI]
• NSC 760389
• IDI1_000283
• NCGC00178692-01
• NCGC00178692-02
• NCGC00178692-04
• NCGC00181086-01
• AC-15988
• CAS-552-79-4
• (1R,2S)-(-)-N-Methylephedrine, 99%
• LS-175608
• FT-0770746
• alpha-[1-(Dimethylamino)ethyl]benzenemethanol
• D08206
• AB00052416_02
• Q2331543
• BRD-K82236108-001-02-3
• BRD-K82236108-001-03-1
• BRD-K82236108-001-04-9
• (R*,S*)-(1)-alpha-(1-(Dimethylamino)ethyl)benzyl alcohol
• Benzenemethanol, alpha-(1-(dimethylamino)ethyl)-, (R-(R*,S*))-
• Methylephedrine ((1R,2S)-Methylephedrine) 1.0 mg/ml in Methanol
• BENZENEMETHANOL, .ALPHA.-((1R)-1-(DIMETHYLAMINO)ETHYL)-, (.ALPHA.S)-REL-
• BENZENEMETHANOL, ALPHA-((1S)-1-(DIMETHYLAMINO)ETHYL)-, (.ALPHA.R)-

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9457	94.57%
Caco-2	+	0.9366	93.66%
Blood Brain Barrier	+	0.9000	90.00%
Human oral bioavailability	+	0.7286	72.86%
Subcellular localzation	Mitochondria	0.5888	58.88%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9498	94.98%
OATP1B3 inhibitior	+	0.9561	95.61%
MATE1 inhibitior	-	0.9800	98.00%
OCT2 inhibitior	-	0.7750	77.50%
BSEP inhibitior	-	0.8758	87.58%
P-glycoprotein inhibitior	-	0.9754	97.54%
P-glycoprotein substrate	-	0.9148	91.48%
CYP3A4 substrate	-	0.7402	74.02%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6565	65.65%
CYP3A4 inhibition	-	0.9423	94.23%
CYP2C9 inhibition	-	0.9653	96.53%
CYP2C19 inhibition	-	0.8849	88.49%
CYP2D6 inhibition	-	0.7228	72.28%
CYP1A2 inhibition	-	0.7171	71.71%
CYP2C8 inhibition	-	0.9975	99.75%
CYP inhibitory promiscuity	-	0.9068	90.68%
UGT catelyzed	+	0.7000	70.00%
Carcinogenicity (binary)	-	0.6620	66.20%
Carcinogenicity (trinary)	Non-required	0.6005	60.05%
Eye corrosion	-	0.7932	79.32%
Eye irritation	-	0.8896	88.96%
Skin irritation	+	0.5000	50.00%
Skin corrosion	+	0.6711	67.11%
Ames mutagenesis	-	0.9100	91.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6382	63.82%
Micronuclear	+	0.5100	51.00%
Hepatotoxicity	-	0.5309	53.09%
skin sensitisation	-	0.8430	84.30%
Respiratory toxicity	+	0.7556	75.56%
Reproductive toxicity	-	0.5222	52.22%
Mitochondrial toxicity	+	0.6250	62.50%
Nephrotoxicity	-	0.7316	73.16%
Acute Oral Toxicity (c)	III	0.4831	48.31%
Estrogen receptor binding	-	0.8749	87.49%
Androgen receptor binding	-	0.6357	63.57%
Thyroid receptor binding	-	0.8305	83.05%
Glucocorticoid receptor binding	-	0.9144	91.44%
Aromatase binding	-	0.9001	90.01%
PPAR gamma	-	0.8714	87.14%
Honey bee toxicity	-	0.9614	96.14%
Biodegradation	-	0.9750	97.50%
Crustacea aquatic toxicity	-	0.5600	56.00%
Fish aquatic toxicity	-	0.8160	81.60%

Targets

Proven Targets:

No proven targets yet!

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL2581	P07339	Cathepsin D	96.35%	98.95%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	92.17%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	90.31%	94.62%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	89.01%	95.56%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	88.69%	94.08%
CHEMBL221	P23219	Cyclooxygenase-1	86.36%	90.17%
CHEMBL3359	P21462	Formyl peptide receptor 1	83.18%	93.56%

Plants that contains it

• Ephedra distachya subsp. helvetica
• Ephedra equisetina
• Ephedra intermedia
• Ephedra sinica
• Zanthoxylum integrifoliolum

Cross-Links

• PubChem: 64782
• NPASS: NPC214200
• LOTUS: LTS0251939
• wikiData: Q105033016