Pseudoephedrine

Details

• Internal ID: 368b3f91-8059-4e46-a0ad-94d09ce259e3
• Taxonomy: Benzenoids > Benzene and substituted derivatives > Phenylpropanes
• IUPAC Name: (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
• SMILES (Canonical): CC(C(C1=CC=CC=C1)O)NC
• SMILES (Isomeric): C[C@@H]([C@H](C1=CC=CC=C1)O)NC
• InChI: InChI=1S/C10H15NO/c1-8(11-2)10(12)9-6-4-3-5-7-9/h3-8,10-12H,1-2H3/t8-,10+/m0/s1
• InChI Key: KWGRBVOPPLSCSI-WCBMZHEXSA-N
• Popularity: 1,211 references in papers

Physical and Chemical Properties

• Molecular Formula: C₁₀H₁₅NO
• Molecular Weight: 165.23 g/mol
• Exact Mass: 165.115364102 g/mol
• Topological Polar Surface Area (TPSA): 32.30 Ų
• XlogP: 0.90
• Atomic LogP (AlogP): 1.33
• H-Bond Acceptor: 2
• H-Bond Donor: 2
• Rotatable Bonds: 3

Synonyms

• (+)-Pseudoephedrine
• Isoephedrine
• d-Pseudoephedrine
• trans-Ephedrine
• d-Isoephedrine
• Psi-ephedrin
• Psi-ephedrine
• (+)-threo-Ephedrine
• d-psi-Ephedrine
• Sudafed
• L(+)-psi-Ephedrine
• 90-82-4
• L-(+)-Pseudoephedrine
• (+)-psi-Ephedrine
• Pseudoefedrina
• Pseudoephedrinum
• (+)-(1S,2S)-Pseudoephedrine
• (1S,2S)-2-(methylamino)-1-phenylpropan-1-ol
• Besan
• (1S,2S)-(+)-Pseudoephedrine
• Pseudoephedrine d-form
• (1S,2S)-Pseudoephedrine
• Neodurasina
• Acunaso
• Pseudoephedrine (D)
• Pseudoephedrine, (+)-
• d-psi-2-Methylamino-1-phenyl-1-propanol
• Pseudoefedrina [INN-Spanish]
• Pseudoephedrinum [INN-Latin]
• psi-Ephedrine, (+)-
• Isoephedrine, d-
• Pseudoephedrine [INN:BAN]
• pseudophedrine sulphate
• Pseudoephedrine Ephedrine
• HSDB 3177
• UNII-7CUC9DDI9F
• 7CUC9DDI9F
• alpha-(1-(Methylamino)ethyl)benzyl alcohol
• Pseudoephedrine, L-(+)-
• EINECS 202-018-6
• Neodurasina (TN)
• Acunaso (TN)
• Afrinol
• CHEBI:51209
• Pseudoephedrine (INN)
• Pseudoephedrine polistirex
• Cenafed
• Decofed
• Genaphed
• Maxenal
• Myfedrine
• Robidrine
• Pseudo
• Pedia Care
• DTXSID0023537
• Benzenemethanol, alpha-(1-(methylamino)ethyl)-, (S-(R*,R*))-
• EC 202-018-6
• (+) threo-2-(methylamino)-1-phenyl-1-propanol
• Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-
• Drixoral N.D.
• Benylin Decongestant
• Sudafed Decongestant
• Efidac/24
• Pseudo-12
• Pseudo 60's
• Eltor 120
• Sudafed (TN)
• Benzenemethanol, .alpha.-[(1S)-1-(methylamino)ethyl]-, (.alpha.S)-
• (1S,2S)-2-methylamino-1-phenylpropan-1-ol
• 1-(S),2-(R)-ERYTHRO-(+)-EPHEDRINE
• Pseudoephedrine sulfate
• PSEUDOEPHEDRINE [INN]
• PSEUDOEPHEDRINE (MART.)
• PSEUDOEPHEDRINE [MART.]
• Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alphaS)-
• 2-(Methylamino)-1-phenyl-1-propanol
• 1-EPHEDRINE
• 649031_ALDRICH
• Drixoral Nasal Decongestant
• pseudoephedrin-
• Sudafed Decongestant 12 Hour
• Benzenemethanol, alpha-[1-(methylamino)ethyl]-, [S-(R*,R*)]-
• BENZENEMETHANOL, .ALPHA.-((1S)-1-(METHYLAMINO)ETHYL)-, (.ALPHA.S)-
• Triaminic AM Decongestant Formula
• (I)-Ephedrin
• Sudafed Decongestant Extra Strength
• ephedrine-(racemic)
• Dimetapp Decongestant Pediatric Drops
• (+) pseudoephedrine
• ( )-Pseudoephedrine
• d-Pseudoephedrine base
• Spectrum_000878
• Triaminic Infant Oral Decongestant Drops
• Spectrum2_001303
• Spectrum3_001771
• Spectrum4_001162
• Spectrum5_000650
• Lopac-E-3250
• PSEUDOEPHEDRINE(D)
• (1S,2S) pseudoephedrine
• D00HHS
• (1s, 2s) pseudoephedrine
• (1S,2S)-2-methylamino-1-phenyl-propan-1-ol
• SCHEMBL4368
• CHEMBL1590
• PSEUDOEPHEDRINE [MI]
• (1S,2S)-2-(methylamino)-1-phenyl-propan-1-ol
• BSPBio_003261
• Efidac 24 PseudoephedrineHcl
• KBioGR_001763
• KBioSS_001358
• BIDD:GT0817
• DivK1c_000451
• PSEUDOEPHEDRINE [HSDB]
• SPBio_001365
• Benzenemethanol, .alpha.-[1-(methylamino)ethyl]-, [S-(R*,R*)]-
• PSEUDOEPHEDRINE [VANDF]
• DTXCID003537
• GTPL7286
• BENZENEMETHANOL, .ALPHA.-(1-(METHYLAMINO)ETHYL)-, (S-(R*,R*))-
• PSEUDOEPHEDRINE [WHO-DD]
• KBio1_000451
• KBio2_001358
• KBio2_003926
• KBio2_006494
• KBio3_002762
• (1s, 2s)-(+)-pseudoephedrine
• R01BA02
• NINDS_000451
• PDSP1_001347
• AKOS025401512
• DB00852
• IDI1_000451
• (1S,2S)-(+)-Pseudoephedrine, 98%
• NCGC00015408-01
• NCGC00178180-01
• NCI60_002955
• SBI-0051498.P003
• LS-125922
• (1S,2S)-2-Methylamino-1-phenyl-1-propanol
• C02765
• D08449
• Q263958
• BRD-K84175871-003-02-2
• EPHEDRINE HYDROCHLORIDE IMPURITY B [EP IMPURITY]
• (alpha S)-alpha-[(1S)-1-(Methylamino)ethyl]benzenemethanol
• Bencenometanol, alfa-[(1s)-1-(metilamino) etil]-, (alfas)-
• (alphaS)-alpha-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL
• (.ALPHA.S)-.ALPHA.-((1R)-1-(METHYLAMINO)ETHYL)BENZENEMETHANOL
• Benzenemethanol, alpha-((1S)-1-(methylamino)ethyl)-, (alpha-S)-(9CI)

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9845	98.45%
Caco-2	+	0.9313	93.13%
Blood Brain Barrier	-	0.8500	85.00%
Human oral bioavailability	+	0.7714	77.14%
Subcellular localzation	Lysosomes	0.5451	54.51%
OATP2B1 inhibitior	-	1.0000	100.00%
OATP1B1 inhibitior	+	0.9566	95.66%
OATP1B3 inhibitior	+	0.9659	96.59%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	0.9750	97.50%
BSEP inhibitior	-	0.9237	92.37%
P-glycoprotein inhibitior	-	0.9741	97.41%
P-glycoprotein substrate	-	0.9308	93.08%
CYP3A4 substrate	-	0.7817	78.17%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.6099	60.99%
CYP3A4 inhibition	-	0.9431	94.31%
CYP2C9 inhibition	-	0.7209	72.09%
CYP2C19 inhibition	-	0.5737	57.37%
CYP2D6 inhibition	+	0.5846	58.46%
CYP1A2 inhibition	-	0.5595	55.95%
CYP2C8 inhibition	-	0.9882	98.82%
CYP inhibitory promiscuity	-	0.9070	90.70%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.6242	62.42%
Carcinogenicity (trinary)	Non-required	0.7401	74.01%
Eye corrosion	-	0.9886	98.86%
Eye irritation	-	0.9696	96.96%
Skin irritation	-	0.5871	58.71%
Skin corrosion	-	0.5499	54.99%
Ames mutagenesis	-	0.9900	99.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.7640	76.40%
Micronuclear	+	0.5600	56.00%
Hepatotoxicity	+	0.6651	66.51%
skin sensitisation	-	0.7718	77.18%
Respiratory toxicity	+	0.9222	92.22%
Reproductive toxicity	-	0.5778	57.78%
Mitochondrial toxicity	+	0.9000	90.00%
Nephrotoxicity	-	0.6496	64.96%
Acute Oral Toxicity (c)	III	0.8940	89.40%
Estrogen receptor binding	-	0.9205	92.05%
Androgen receptor binding	-	0.8448	84.48%
Thyroid receptor binding	-	0.8826	88.26%
Glucocorticoid receptor binding	-	0.9120	91.20%
Aromatase binding	-	0.8514	85.14%
PPAR gamma	-	0.9004	90.04%
Honey bee toxicity	-	0.9411	94.11%
Biodegradation	-	0.9500	95.00%
Crustacea aquatic toxicity	-	0.5200	52.00%
Fish aquatic toxicity	-	0.8469	84.69%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL2524	P06280	Alpha-galactosidase A	39810.7 nM; 25118.9 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL3687	P18054	Arachidonate 12-lipoxygenase	3162.3 nM	Potency	via CMAUP
CHEMBL2903	P16050	Arachidonate 15-lipoxygenase	398.1 nM; 398.1 nM	Potency; Potency	via CMAUP; via Super-PRED
CHEMBL3622	P33261	Cytochrome P450 2C19	1584.9 nM	Potency	via CMAUP
CHEMBL3397	P11712	Cytochrome P450 2C9	794.3 nM	Potency	via CMAUP
CHEMBL289	P10635	Cytochrome P450 2D6	12589.3 nM	Potency	via CMAUP
CHEMBL340	P08684	Cytochrome P450 3A4	19952.6 nM; 19952.6 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	631 nM; 1584.9 nM; 631 nM	Potency; Potency; Potency	via CMAUP; via CMAUP; via Super-PRED
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	28183.8 nM; 28183.8 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1075189	P14618	Pyruvate kinase isozymes M1/M2	7943.3 nM; 7943.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1293256	P40225	Thrombopoietin	3162.3 nM; 3162.3 nM	Potency; Potency	via CMAUP; via CMAUP
CHEMBL1963	P16473	Thyroid stimulating hormone receptor	125.9 nM; 125.9 nM	Potency; Potency	via CMAUP; via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL221	P23219	Cyclooxygenase-1	95.30%	90.17%
CHEMBL2581	P07339	Cathepsin D	92.40%	98.95%
CHEMBL3108638	O15164	Transcription intermediary factor 1-alpha	86.30%	95.56%
CHEMBL4208	P20618	Proteasome component C5	85.66%	90.00%
CHEMBL3902	P09211	Glutathione S-transferase Pi	85.00%	93.81%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	84.58%	85.14%
CHEMBL1821	P08173	Muscarinic acetylcholine receptor M4	84.03%	94.08%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	83.32%	96.09%
CHEMBL2035	P08912	Muscarinic acetylcholine receptor M5	82.94%	94.62%
CHEMBL2535	P11166	Glucose transporter	82.59%	98.75%
CHEMBL3401	O75469	Pregnane X receptor	81.47%	94.73%
CHEMBL5284	Q96RR4	CaM-kinase kinase beta	80.16%	89.23%

Plants that contains it

• Ephedra californica
• Ephedra distachya
• Ephedra distachya subsp. helvetica
• Ephedra equisetina
• Ephedra intermedia
• Ephedra minuta
• Ephedra sinica
• Sophora flavescens

Cross-Links

• PubChem: 7028
• NPASS: NPC147000
• ChEMBL: CHEMBL1590
• LOTUS: LTS0007631
• wikiData: Q263958