Racepinephrine

Details

• Internal ID: c0852be1-c8ab-49f7-b712-fd9de6960c54
• Taxonomy: Benzenoids > Phenols > Benzenediols > Catechols
• IUPAC Name: 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• SMILES (Canonical): CNCC(C1=CC(=C(C=C1)O)O)O
• SMILES (Isomeric): CNCC(C1=CC(=C(C=C1)O)O)O
• InChI: InChI=1S/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H3
• InChI Key: UCTWMZQNUQWSLP-UHFFFAOYSA-N
• Popularity: 3,363 references in papers

Physical and Chemical Properties

• Molecular Formula: C₉H₁₃NO₃
• Molecular Weight: 183.20 g/mol
• Exact Mass: 183.08954328 g/mol
• Topological Polar Surface Area (TPSA): 72.70 Ų
• XlogP: -1.40
• Atomic LogP (AlogP): 0.35
• H-Bond Acceptor: 4
• H-Bond Donor: 4
• Rotatable Bonds: 3

Synonyms

• 329-65-7
• dl-Epinephrine
• Racepinephrine
• Racepinefrine
• Epirenamine
• Epinephrine racemic
• (+-)-Adrenaline
• Racepinefrina
• Racepinefrinum
• L(-)-Epinephrine
• (+-)-Epinephrine
• DL-Adrenalin
• 4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
• Vaponefrin
• Epinephrine dl-
• D-Epinephrine
• Epinephrine, dl-
• Racemic Epinephrine
• Epinephrine dl-form
• (+/-)-adrenaline
• 2-(Methylamino)-1-(3,4-dihydroxyphenyl)ethanol
• 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
• UNII-GR0L9S3J0F
• Racemic adrenaline
• EINECS 206-347-6
• Racepinefrinum [INN-Latin]
• GR0L9S3J0F
• Adrenaline, racemic
• Racepinefrina [INN-Spanish]
• 1-(3,4-Dihydroxy)phenyl-2-methylaminoethanol
• d-Adrenaline
• Epinephrine, Racemic
• BRN 2212160
• CCRIS 8140
• Racepinefrine [INN]
• Racepinephrine [USP]
• (+/-)-Epinephrine
• CHEBI:33568
• Alipogene tiparvovec
• CHEMBL1740
• Micronefrin
• 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-
• rac Epinephrine
• DTXSID80858965
• 4-13-00-02927 (Beilstein Handbook Reference)
• ( )-Epinephrine
• L-(+)-Adrenaline
• 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-
• Racepinephrine (USP)
• (+/-)-epinephrine-2,5,6,alpha,beta,beta-d6
• Racepinefrinum (INN-Latin)
• Racepinefrina (INN-Spanish)
• Micronephrine
• MLS001333244
• RACEPINEPHRINE (USP MONOGRAPH)
• RACEPINEPHRINE [USP MONOGRAPH]
• 929881-05-0
• BRN 2938799
• L-(-)-EPINEPHRINE
• (+/-)-Epinephrine;DL-Adrenaline;(+/-)-Adrenaline
• SMR000058236
• Epinepherine
• DL-Adrenali
• Adrenaline,(S)
• Epinephrine dl form
• (plusmn)-adrenaline
• (+-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
• (R,S)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzylalkohol
• EPINEPHRINE,(+)
• (.+/-.)-Adrenaline
• (.+/-.)-Epinephrine
• 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol #
• Racepinephrine (USP/INN)
• AROCLOR1016
• cid_5924
• SCHEMBL3815
• (r)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
• Hydrochloride, racepinephrine
• NCIOpen2_000082
• Lopac0_000522
• GTPL509
• RACEPINEFRINE [WHO-DD]
• 4-(1-Hydroxy-2-methylamino-ethyl)-benzene-1,2-diol
• SGCUT00008
• (-)-Epinephrine (+)-bitartrate salt;L-Adrenaline (+)-bitartrate salt
• BDBM84342
• DTXCID20196651
• EPINEPHRINE DL-FORM [MI]
• CHEBI:194548
• (+/-)-Epinephrine, >=95%
• HMS3259B19
• HMS3656E12
• 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (+-)-
• 104655-05-2
• BCP17220
• HY-B0447
• to_000046
• AC-395
• Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (+-)-
• PDSP1_000587
• PDSP2_000584
• s2523
• AKOS005721043
• CCG-204612
• NC00671
• SDCCGSBI-0050505.P002
• BRN-2938799
• ( inverted exclamation markA)-Adrenaline
• NCGC00015417-02
• NCGC00015417-03
• NCGC00015417-16
• NCGC00162177-01
• ( inverted exclamation markA)-Epinephrine
• AS-12580
• ()-Epinephrine;DL-Adrenaline;()-Adrenaline
• A0172
• FT-0625455
• FT-0695432
• D05688
• D88221
• EN300-208482
• AB00514461_07
• A821533
• L000877
• 4-(1-hydroxy-2-methylaminoethyl)benzene-1,2-diol
• J-018952
• Q7279006
• SR-01000075862-8
• 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol, 1
• 9561B8BB-366F-4A33-B295-1C6E682AC6BB
• (.+/-.)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
• 4-[1-hydroxy-2-(methylamino)ethyl]pyrocatechol;hydrochloride
• (.+/-.)-3,4-Dihydroxy-.alpha.-[(methylamino)methyl]benzyl alcohol
• 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-, (.+/-.)-
• 4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;DL-Adrenaline
• 4-[2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol;hydrochloride
• Benzyl alcohol, 3,4-dihydroxy-.alpha.-((methylamino)methyl)-, (.+/-.)-
• BENZYL ALCOHOL, 3,4-DIHYDROXY-alpha-((METHYLAMINO)METHYL)-, (+/-)-
• BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (+/-)-
• InChI=1/C9H13NO3/c1-10-5-9(13)6-2-3-7(11)8(12)4-6/h2-4,9-13H,5H2,1H
• 8060-13-7

2D Structure

ADMET Properties (via admetSAR 2)

Target	Value	Probability (raw)	Probability (%)
Human Intestinal Absorption	+	0.9802	98.02%
Caco-2	-	0.9373	93.73%
Blood Brain Barrier	-	0.7000	70.00%
Human oral bioavailability	-	0.5571	55.71%
Subcellular localzation	Mitochondria	0.7131	71.31%
OATP2B1 inhibitior	-	0.8625	86.25%
OATP1B1 inhibitior	+	0.9457	94.57%
OATP1B3 inhibitior	+	0.9588	95.88%
MATE1 inhibitior	-	1.0000	100.00%
OCT2 inhibitior	-	1.0000	100.00%
BSEP inhibitior	-	0.9880	98.80%
P-glycoprotein inhibitior	-	0.9810	98.10%
P-glycoprotein substrate	-	0.9363	93.63%
CYP3A4 substrate	-	0.7865	78.65%
CYP2C9 substrate	-	1.0000	100.00%
CYP2D6 substrate	+	0.5000	50.00%
CYP3A4 inhibition	-	0.9121	91.21%
CYP2C9 inhibition	-	0.9563	95.63%
CYP2C19 inhibition	-	0.9451	94.51%
CYP2D6 inhibition	-	0.9638	96.38%
CYP1A2 inhibition	-	0.7862	78.62%
CYP2C8 inhibition	-	0.9609	96.09%
CYP inhibitory promiscuity	-	0.9516	95.16%
UGT catelyzed	+	0.8000	80.00%
Carcinogenicity (binary)	-	0.8108	81.08%
Carcinogenicity (trinary)	Non-required	0.7037	70.37%
Eye corrosion	-	0.8952	89.52%
Eye irritation	-	0.9541	95.41%
Skin irritation	-	0.6097	60.97%
Skin corrosion	-	0.6947	69.47%
Ames mutagenesis	-	0.9800	98.00%
Human Ether-a-go-go-Related Gene inhibition	-	0.6998	69.98%
Micronuclear	-	0.6968	69.68%
Hepatotoxicity	-	0.7875	78.75%
skin sensitisation	-	0.5367	53.67%
Respiratory toxicity	+	0.9778	97.78%
Reproductive toxicity	+	0.7889	78.89%
Mitochondrial toxicity	+	1.0000	100.00%
Nephrotoxicity	-	0.8507	85.07%
Acute Oral Toxicity (c)	II	0.5282	52.82%
Estrogen receptor binding	-	0.8012	80.12%
Androgen receptor binding	-	0.7439	74.39%
Thyroid receptor binding	-	0.5318	53.18%
Glucocorticoid receptor binding	-	0.6491	64.91%
Aromatase binding	-	0.8033	80.33%
PPAR gamma	-	0.9017	90.17%
Honey bee toxicity	-	0.8548	85.48%
Biodegradation	-	0.6250	62.50%
Crustacea aquatic toxicity	-	0.6100	61.00%
Fish aquatic toxicity	-	0.8636	86.36%

Targets

Proven Targets:

CHEMBL ID	UniProt ID	Name	Min activity	Assay type	Source
CHEMBL232	P35368	Alpha-1b adrenergic receptor	75 nM	EC50	via Super-PRED
CHEMBL213	P08588	Beta-1 adrenergic receptor	290 nM	EC50	via Super-PRED
CHEMBL210	P07550	Beta-2 adrenergic receptor	360 nM	Ki	via Super-PRED
CHEMBL246	P13945	Beta-3 adrenergic receptor	31 nM	EC50	via Super-PRED
CHEMBL217	P14416	Dopamine D2 receptor	910 nM	Ki	via Super-PRED
CHEMBL4159	Q99714	Endoplasmic reticulum-associated amyloid beta-peptide-binding protein	794.3 nM	Potency	via Super-PRED
CHEMBL1075138	Q9NUW8	Tyrosyl-DNA phosphodiesterase 1	794.3 nM	Potency	via Super-PRED

Predicted Targets (via Super-PRED):

CHEMBL ID	UniProt ID	Name	Probability	Model accuracy
CHEMBL5619	P27695	DNA-(apurinic or apyrimidinic site) lyase	98.10%	91.11%
CHEMBL4261	Q16665	Hypoxia-inducible factor 1 alpha	95.97%	85.14%
CHEMBL3251	P19838	Nuclear factor NF-kappa-B p105 subunit	94.35%	96.09%
CHEMBL2581	P07339	Cathepsin D	92.22%	98.95%
CHEMBL1951	P21397	Monoamine oxidase A	88.58%	91.49%
CHEMBL1860	P10827	Thyroid hormone receptor alpha	87.78%	99.15%
CHEMBL3401	O75469	Pregnane X receptor	87.11%	94.73%
CHEMBL4208	P20618	Proteasome component C5	87.09%	90.00%
CHEMBL4203	Q9HAZ1	Dual specificity protein kinase CLK4	84.15%	94.45%

Plants that contains it

• Scoparia dulcis

Cross-Links

• PubChem: 838
• LOTUS: LTS0003906
• wikiData: Q7279006