| In ZINC since | Heavy atoms | Benign functionality |
|---|---|---|
| September 30th, 2005 | 13 | No |
Popular Name: L-Adrenaline L-Adrenaline
Find On: PubMed — Wikipedia — Google
CAS Numbers: 329-63-5 , 329-65-7 , 51-42-3 , 51-43-4 , 6912-68-1 , [329-63-5] , [51-43-4] , [55-31-2]
(+/-)-Epinephrine hydrochloride; 329-63-5; CPD000857209; SAM002699891
(+/-)-Epinephrine hydrochloride; CPD000857209; Racemic Epinephrine; SAM002699891
(-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
(-)-Epinephrine (+)-bitartrate salt
(-)-Epinephrine (+)-bitartrate salt, 98+%
(R)-(_)-3,4-Dihydroxy-_-(methylaminomethyl)benzyl alcohol
(R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
(R)-adrenaline cation; L-epinephrine cation; L-epinephrine(1+); R-adrenaline
1,2-Benzenediol, 4-((1R)-1-hydroxy-2-(methylamino)ethyl)-
1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-
1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-
1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
4-((R)-1-Hydroxy-2-methylamino-ethyl)-benzene-1,2-diol
4-(1-Hydroxy-2-(methylamino)ethyl)-1,2-benzenediol
4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
4-(1-Hydroxy-2-(methylamino)ethyl)benzene-1,2-diol hydrochloride
4-(1-hydroxy-2-methylamino-ethyl)benzene-1,2-diol
4-[(1R)-1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
4-[1-HYDROXY-2-(METHYLAMINO)ETHYL]-1,2-BENZENEDIOL HYDROCHLORIDE
4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
51-42-3; Asmatane mist (TN); D02149; Epinephrine bitartrate (JAN/USP); Medihaler-epi (TN)
Adrenalin; Epipen; Epipen JR; Primatene
Adrenaline (BAN); Epinephrine (FDA
Bupivacaine Hcl and Epinephrine
D02149, Adrenalinetartrate, Adrenaline tatrate, Epinephrine Acid Tartrate
D05689; Racepinephrine hydrochloride (USP)
epinefrina; epinephrine; epinephrinum
Epinephrine bitartrate (Adrenalinium)
FDA); Epinephrine Bitartrate (FDA
l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
L-adrenaline hydrochloride; L-epinephrine hydrochloride; epinephrine hydrochloride
L-epinephrine; adrenaline; epinephrine
Levo-Methylaminoethanolcatechol
Racepinefrine (INN); Racepinephrine (USP); Racepinephrine HCl (USP)
Racepinefrine (INN); Racepinephrine (USP); Racepinephrine Hydrochloride (USP)
USP); Epinephrine Bitartrate (FDA
USP); Epinephrine HCl (JAN); Epinephrine Bitartrate (FDA
| Type pH range | xlogP | Des A‑Pol Apolar desolvation (kcal/mol) | Des Pol Polar desolvation (kcal/mol) | H Don H-bond donors | H Acc H-bond acceptors | Chg Net charge | tPSA (Ų) | MWT Molecular weight (g/mol) | RB Rotatable bonds | DL |
|---|---|---|---|---|---|---|---|---|---|---|
| Ref Reference (pH 7) | -0.06 | -2.8 | -45.1 | 5 | 4 | 1 | 77 | 184.215 | 3 | ↓ |
| Hi High (pH 8-9.5) | -0.06 | -4.26 | -7.35 | 4 | 4 | 0 | 73 | 183.207 | 3 | ↓ |
| Note Type | Comments | Provided By |
|---|---|---|
| ALOGPS_SOLUBILITY | 1.86e+01 g/l | DrugBank-approved |
| Mp [°C] | 155 | Acros Organics |
| Mp [°C] | 208 - 211 | Acros Organics |
| Melting_Point | 216-219? | Alfa-Aesar |
| Melting_Point | 216-219° | Alfa-Aesar |
| purity | 9.500000000000000e+001 | Enamine Building Blocks Enamine Building Blocks |
| Purity | 95% | Fluorochem |
| UniProt Database Links | ADA2A_DANRE; ADA2A_HUMAN; ADRB1_BOVIN; ADRB1_CANFA; ADRB1_FELCA; ADRB1_HUMAN; ADRB1_MACMU; ADRB1_MELGA; ADRB1_MERUN; ADRB1_MOUSE; ADRB1_PIG; ADRB1_RAT; ADRB1_SHEEP; ADRB2_BOVIN; ADRB2_CANFA; ADRB2_FELCA; ADRB2_HUMAN; ADRB2_MACMU; ADRB2_MERUN; ADRB2_MESAU | ChEBI |
| Target | Adrenergic Receptor | Selleck Chemicals |
| H phrase | H315: Causes skin irritation | Acros Organics |
| H phrase | H315: Causes skin irritation; H331: Toxic if inhaled; H301: Toxic if swallowed; H311: Toxic in contact with skin; H319: Causes serious eye irritation; H335: May cause respiratory irritation; H412: Harmful to aquatic life with long lasting effects; H373: M | Acros Organics |
| H phrase | H335: May cause respiratory irritation | Acros Organics |
| H phrase | H335: May cause respiratory irritation; H315: Causes skin irritation; H300: Fatal if swallowed; H319: Causes serious eye irritation | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | NCC_SAMPLE_SUPPLIER : LightBiologicals; NCC_SUPPLIER_STRUCTURE_ID : MZ-3008; NCC_SUPPLIER_SAMPLE_COMMENTS : SLIGHT COFFEE POWDER | NIH Clinical Collection via PubChem |
| mechanism | Neurotransmitter | IBScreen Bioactives |
| biological_use | Ophthalmic adrenergic agent | IBScreen Bioactives |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician | Acros Organics |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician; P261: Avoid breathing dust/fume/gas/mist/vapors/spray; P302+ P352: IF ON SKIN: Wash with plenty of soap and water; P280: Wear protective gloves/protective clothing/eye protec | Acros Organics |
| P phrase | P301 + P310: IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician; P280: Wear protective gloves/protective clothing/eye protection/face protection; P312: Call a POISON CENTER or doctor/physician if you feel unwell; P302 + P350: IF ON SKIN: G | Acros Organics |
| UniProt Database Links | PNMT_BOVIN; PNMT_HUMAN; PNMT_MOUSE; PNMT_PIG; PNMT_RAT | ChEBI |
| R phrase | R23/24/25: Toxic by inhalation, in contact with skin and if swallowed. | Acros Organics |
| R phrase | R23/24/25: Toxic by inhalation, in contact with skin and if swallowed.; R33: Danger of cumulative effects.; R36/37/38: Irritating to eyes, respiratory system and skin.; R52/53: Harmful to aquatic organisms, may cause long-term adverse effects in the aquat | Acros Organics |
| R phrase | R28: Very toxic if swallowed. | Acros Organics |
| R phrase | R28: Very toxic if swallowed.; R36/37/38: Irritating to eyes, respiratory system and skin. | Acros Organics |
| Reactome Database Links | REACT_15291; REACT_15442; REACT_15538; REACT_16893; REACT_16992; REACT_17002; REACT_17008; REACT_18370; REACT_20519; REACT_22150; REACT_22170; REACT_22188; REACT_22221; REACT_22234; REACT_22239; REACT_22263; REACT_22264; REACT_22268; REACT_22283; REACT_22 | ChEBI |
| S phrase | S23: Do not breathe gas/fumes/vapour/spray. | Acros Organics |
| S phrase | S23: Do not breathe gas/fumes/vapour/spray.; S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.; S45: In case of accident or if | Acros Organics |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice. | Acros Organics |
| S phrase | S26: In case of contact with eyes, rinse immediately with plenty of water and seek medical advice.; S28A: After contact with skin, wash immediately with plenty of water.; S36/37/39: Wear suitable protective clothing, gloves and eye/face protection.; S45: | Acros Organics |
| PUBCHEM_SUBSTANCE_COMMENT | SAMPLE_SUPPLIER: LightBiologicals; SUPPLIER_STRUCTURE_ID: MZ-3008; SUPPLIER_COMMENTS: SLIGHT COFFEE POWDER | NIH Clinical Collection via PubChem |
| Hazard | T+: Very toxic | Acros Organics |
| Hazard | T: Toxic | Acros Organics |
| Target | Transforming growth factor beta-1(P01137)&Platelet-derived growth factor subunit B(P01127)&Carnitine O-acetyltransferase(P43155)&Vascular endothelial growth factor A(P15692)&Tumor necrosis factor(P01375)&Interleukin-6(P05231)&Insulin-like growth factor 1 | Herbal Ingredients Targets |
| Code | Description | Organism Class | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| ADA1A-3-E | Alpha-1a Adrenergic Receptor (cluster #3 Of 3), Eukaryotic | Eukaryotes | 17 | 0.84 | Binding ≤ 10μM |
| ADA1B-1-E | Alpha-1b Adrenergic Receptor (cluster #1 Of 4), Eukaryotic | Eukaryotes | 17 | 0.84 | Binding ≤ 10μM |
| ADA1D-1-E | Alpha-1d Adrenergic Receptor (cluster #1 Of 3), Eukaryotic | Eukaryotes | 17 | 0.84 | Binding ≤ 10μM |
| ADA2A-3-E | Alpha-2a Adrenergic Receptor (cluster #3 Of 4), Eukaryotic | Eukaryotes | 38 | 0.80 | Binding ≤ 10μM |
| ADA2B-4-E | Alpha-2b Adrenergic Receptor (cluster #4 Of 4), Eukaryotic | Eukaryotes | 38 | 0.80 | Binding ≤ 10μM |
| ADA2C-3-E | Alpha-2c Adrenergic Receptor (cluster #3 Of 4), Eukaryotic | Eukaryotes | 38 | 0.80 | Binding ≤ 10μM |
| ADRB1-1-E | Beta-1 Adrenergic Receptor (cluster #1 Of 2), Eukaryotic | Eukaryotes | 2100 | 0.61 | Binding ≤ 10μM |
| ADRB2-1-E | Beta-2 Adrenergic Receptor (cluster #1 Of 2), Eukaryotic | Eukaryotes | 720 | 0.66 | Binding ≤ 10μM |
| OPRM-1-E | Mu-type Opioid Receptor (cluster #1 Of 4), Eukaryotic | Eukaryotes | 4000 | 0.58 | Binding ≤ 10μM |
| ADA1A-1-E | Alpha-1a Adrenergic Receptor (cluster #1 Of 2), Eukaryotic | Eukaryotes | 400 | 0.69 | Functional ≤ 10μM |
| ADA2A-3-E | Alpha-2a Adrenergic Receptor (cluster #3 Of 3), Eukaryotic | Eukaryotes | 300 | 0.70 | Functional ≤ 10μM |
| ADA2B-2-E | Alpha-2b Adrenergic Receptor (cluster #2 Of 3), Eukaryotic | Eukaryotes | 300 | 0.70 | Functional ≤ 10μM |
| ADA2C-3-E | Alpha-2c Adrenergic Receptor (cluster #3 Of 3), Eukaryotic | Eukaryotes | 300 | 0.70 | Functional ≤ 10μM |
| ADRB1-1-E | Beta-1 Adrenergic Receptor (cluster #1 Of 1), Eukaryotic | Eukaryotes | 230 | 0.71 | Functional ≤ 10μM |
| ADRB2-1-E | Beta-2 Adrenergic Receptor (cluster #1 Of 2), Eukaryotic | Eukaryotes | 230 | 0.71 | Functional ≤ 10μM |
| ADRB3-1-E | Beta-3 Adrenergic Receptor (cluster #1 Of 1), Eukaryotic | Eukaryotes | 230 | 0.71 | Functional ≤ 10μM |
| Z104304-1-O | Adrenergic Receptor Alpha-1 (cluster #1 Of 3), Other | Other | 2800 | 0.60 | Binding ≤ 10μM |
| Z104304-1-O | Adrenergic Receptor Alpha-1 (cluster #1 Of 1), Other | Other | 4073 | 0.58 | Functional ≤ 10μM |
| Z50512-1-O | Cavia Porcellus (cluster #1 Of 7), Other | Other | 400 | 0.69 | Functional ≤ 10μM |
| Uniprot | Swissprot | Description | Affinity (nM) | LE (kcal/mol/atom) | Type |
|---|---|---|---|---|---|
| Z104304 | Z104304 | Adrenergic Receptor Alpha-1 | 200 | 0.72 | Binding ≤ 1μM |
| ADA1A_RAT | P43140 | Alpha-1a Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 1μM |
| ADA1B_RAT | P15823 | Alpha-1b Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 1μM |
| ADA1D_RAT | P23944 | Alpha-1d Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 1μM |
| ADA2A_HUMAN | P08913 | Alpha-2a Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 1μM |
| ADA2A_RAT | P22909 | Alpha-2a Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 1μM |
| ADA2B_RAT | P19328 | Alpha-2b Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 1μM |
| ADA2B_HUMAN | P18089 | Alpha-2b Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 1μM |
| ADA2C_RAT | P22086 | Alpha-2c Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 1μM |
| ADA2C_HUMAN | P18825 | Alpha-2c Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 1μM |
| ADRB2_HUMAN | P07550 | Beta-2 Adrenergic Receptor, Human | 630 | 0.67 | Binding ≤ 1μM |
| ADRB2_CANFA | P54833 | Beta-2 Adrenergic Receptor, Canine | 660 | 0.67 | Binding ≤ 1μM |
| Z104304 | Z104304 | Adrenergic Receptor Alpha-1 | 1600 | 0.62 | Binding ≤ 10μM |
| ADA1A_RAT | P43140 | Alpha-1a Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 10μM |
| ADA1A_HUMAN | P35348 | Alpha-1a Adrenergic Receptor, Human | 2000 | 0.61 | Binding ≤ 10μM |
| ADA1B_RAT | P15823 | Alpha-1b Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 10μM |
| ADA1D_RAT | P23944 | Alpha-1d Adrenergic Receptor, Rat | 17 | 0.84 | Binding ≤ 10μM |
| ADA2A_HUMAN | P08913 | Alpha-2a Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 10μM |
| ADA2A_RAT | P22909 | Alpha-2a Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 10μM |
| ADA2B_RAT | P19328 | Alpha-2b Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 10μM |
| ADA2B_HUMAN | P18089 | Alpha-2b Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 10μM |
| ADA2C_RAT | P22086 | Alpha-2c Adrenergic Receptor, Rat | 13 | 0.85 | Binding ≤ 10μM |
| ADA2C_HUMAN | P18825 | Alpha-2c Adrenergic Receptor, Human | 5 | 0.89 | Binding ≤ 10μM |
| ADRB1_RAT | P18090 | Beta-1 Adrenergic Receptor, Rat | 1100 | 0.64 | Binding ≤ 10μM |
| ADRB1_HUMAN | P08588 | Beta-1 Adrenergic Receptor, Human | 3000 | 0.59 | Binding ≤ 10μM |
| ADRB2_CANFA | P54833 | Beta-2 Adrenergic Receptor, Canine | 1100 | 0.64 | Binding ≤ 10μM |
| ADRB2_HUMAN | P07550 | Beta-2 Adrenergic Receptor, Human | 630 | 0.67 | Binding ≤ 10μM |
| OPRM_RAT | P33535 | Mu Opioid Receptor, Rat | 4000 | 0.58 | Binding ≤ 10μM |
| Z104304 | Z104304 | Adrenergic Receptor Alpha-1 | 4073 | 0.58 | Functional ≤ 10μM |
| ADA1A_HUMAN | P35348 | Alpha-1a Adrenergic Receptor, Human | 400 | 0.69 | Functional ≤ 10μM |
| ADA2A_HUMAN | P08913 | Alpha-2a Adrenergic Receptor, Human | 300 | 0.70 | Functional ≤ 10μM |
| ADA2B_HUMAN | P18089 | Alpha-2b Adrenergic Receptor, Human | 300 | 0.70 | Functional ≤ 10μM |
| ADA2C_HUMAN | P18825 | Alpha-2c Adrenergic Receptor, Human | 300 | 0.70 | Functional ≤ 10μM |
| ADRB1_HUMAN | P08588 | Beta-1 Adrenergic Receptor, Human | 15 | 0.84 | Functional ≤ 10μM |
| ADRB1_RAT | P18090 | Beta-1 Adrenergic Receptor, Rat | 230 | 0.71 | Functional ≤ 10μM |
| ADRB2_HUMAN | P07550 | Beta-2 Adrenergic Receptor, Human | 15 | 0.84 | Functional ≤ 10μM |
| ADRB2_CANFA | P54833 | Beta-2 Adrenergic Receptor, Canine | 230 | 0.71 | Functional ≤ 10μM |
| ADRB2_RAT | P10608 | Beta-2 Adrenergic Receptor, Rat | 230 | 0.71 | Functional ≤ 10μM |
| ADRB3_RAT | P26255 | Beta-3 Adrenergic Receptor, Rat | 230 | 0.71 | Functional ≤ 10μM |
| ADRB3_HUMAN | P13945 | Beta-3 Adrenergic Receptor, Human | 31 | 0.81 | Functional ≤ 10μM |
| Z50512 | Z50512 | Cavia Porcellus | 400 | 0.69 | Functional ≤ 10μM |
| Description | Species |
|---|---|
| Adrenaline signalling through Alpha-2 adrenergic receptor | |
| Adrenaline,noradrenaline inhibits insulin secretion | |
| Adrenoceptors | |
| Catecholamine biosynthesis | |
| G alpha (12/13) signalling events | |
| G alpha (i) signalling events | |
| G alpha (q) signalling events | |
| G alpha (s) signalling events | |
| G alpha (z) signalling events | |
| Na+/Cl- dependent neurotransmitter transporters | |
| Organic cation transport | |
| Transport of nucleosides and free purine and pyrimidine bases across the plasma |
| Description | Species |
|---|---|
| Adrenaline signalling through Alpha-2 adrenergic receptor | |
| Adrenaline,noradrenaline inhibits insulin secretion | |
| Adrenoceptors | |
| G alpha (12/13) signalling events | |
| G alpha (i) signalling events | |
| G alpha (q) signalling events | |
| G alpha (s) signalling events | |
| G alpha (z) signalling events | |
| G-protein activation | |
| Opioid Signalling | |
| Peptide ligand-binding receptors |
