Epinephrine

A summary of the most common chemical descriptors (InChI Key and SMILES codes) for Epinephrine are summarized together with 3D and 2D structures and relevant physico-chemical properties.

What is the Epinephrine?

The molecule Epinephrine presents a molecular formula of C35H36ClNO3S and its IUPAC name is 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol.

Epinephrine is a molecule that plays an important role in the body's fight-or-flight response. When the body is under stress, epinephrine is released into the bloodstream, where it increases heart rate and blood pressure and prepares the body for physical activity. Epinephrine also has a number of other effects, including dilating the airways and increasing blood sugar levels..

Epinephrine is produced by the adrenal glands, which are located just above the kidneys. The release of epinephrine is controlled by the nervous system, and it is released in response to stressors such as fear, exercise, or anxiety. Epinephrine is also released in response to low blood sugar levels, and it helps to raise blood sugar levels by increasing the release of glucose from the liver..

Epinephrine has a number of side effects, including anxiety, shaking, and sweating. It can also cause heart palpitations and an irregular heartbeat. In some people, epinephrine can trigger a dangerous condition called supraventricular tachycardia, which is a rapid heart rate that can be fatal..

If you are experiencing any of these side effects, you should seek medical help immediately. Epinephrine is a powerful molecule that can save your life in an emergency, but it should be used with caution..

3D structure

Cartesian coordinates

Geometry of Epinephrine in x, y and z coordinates (Å units) to copy/paste elsewhere. Generated with Open Babel software.

2D drawing

 

Epinephrine UCHDWCPVSPXUMX-TZIWLTJVSA-N chemical compound 2D structure molecule svg
Epinephrine

 

Molecule descriptors

 
IUPAC name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
InChI codeInChI=1S/C35H36ClNO3S/c1-34(2,40)30-9-4-3-7-25(30)13-17-32(41-23-35(18-19-35)22-33(38)39)27-8-5-6-24(20-27)10-15-29-16-12-26-11-14-28(36)21-31(26)37-29/h3-12,14-16,20-21,32,40H,13,17-19,22-23H2,1-2H3,(H,38,39)/b15-10+/t32-/m1/s1
InChI KeyUCHDWCPVSPXUMX-TZIWLTJVSA-N
SMILESCC(C)(O)c1ccccc1CC[C@@H](SCC1(CC(=O)O)CC1)c1cccc(/C=C/c2ccc3ccc(Cl)cc3n2)c1

Other names (synonyms)

IUPAC nomenclature provides a standardized method for naming chemical compounds. Although this system is widely used in chemistry, many chemical compounds have also other names commonly used in different contexts. These synonyms can come from a variety of sources and are used for a variety of purposes.

One common source of synonyms for chemical compounds is the common or trivial names, assigned on the basis of appearance, properties, or origin of the molecule.

Another source of synonyms are historical or obsolete names employed in the past, however replaced nowadays by more modern or standardized names.

In addition to common and historical names, chemical compounds may also have synonyms that are specific to a particular field or industry.

  • (-)-(R)-Epinephrine
  • (-)-3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)BENZYL ALCOHOL
  • (-)-3,4-Dihydroxy-a-[2-(methylamino)ethyl]benzyl alcohol
  • (-)-3,4-Dihydroxy-alpha-((methylamino)methyl)benzyl alcohol
  • (-)-3,4-Dihydroxy-alpha-[2-(methylamino)ethyl]benzyl alcohol
  • (-)-3,4-dihydroxy-a-[(methylamino)methyl]-Benzyl alcohol
  • (-)-3,4-dihydroxy-alpha-[(methylamino)methyl]-Benzyl alcohol
  • (-)-Adrenaline
  • (-)-Epinephrine
  • (-)-Epinephrine;L-Adrenaline;(-)-Adrenalin
  • (-)-R-Epinephrine
  • (R)-(-)-Adnephrine
  • (R)-(-)-Adrenaline
  • (R)-(-)-Epinephrine
  • (R)-(-)-Epirenamine
  • (R)-4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol
  • (R)-Adrenaline
  • (R)-Epinephrine
  • (r)-4-(1-hydroxy-2-(methylamino)ethyl)benzene-1,2-diol
  • 1,2-Benzenediol, 4-((1R)-1-hydroxy-2-(methylamino)ethyl)-
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (R)-
  • 1,2-Benzenediol, 4-(1-hydroxy-2-(methylamino)ethyl)-, (theta)-
  • 1,2-Benzenediol, 4-[(1R)-1-hydroxy-2-(methylamino)ethyl]-
  • 1,2-Benzenediol, 4-[1-hydroxy-2-(methylamino)ethyl]-, (R)-
  • 1-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
  • 1-Adrenalin
  • 1-Epinephrine
  • 104655-05-2
  • 2,3-bis(oxidanyl)butanedioic acid;4-[(1R)-2-(methylamino)-1-oxidanyl-ethyl]benzene-1,2-diol
  • 2,3-dihydroxybutanedioic acid;4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
  • 3,4-Dihydroxy-.alpha.-((methylamino)methyl)benzyl alcohol
  • 4,5-beta-trihydroxy-N-methylphenethylamine
  • 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)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-[(1R)-1-hydroxy-2-(methylamino)ethyl]pyrocatechol;tartaric acid
  • 4-[(1R)-1-hydroxy-2-methylaminoethyl]benzene-1,2-diol
  • 4-[1-Hydroxy-2-(methylamino)ethyl]-1,2-benzenediol #
  • 51-43-4
  • 51-43-4 (FREE BASE)
  • A0173
  • AB00573227-11
  • AB00573227-12
  • AB00573227-13
  • AB00573227_14
  • AB00573227_15
  • AC-13188
  • AC-31211
  • ADROP
  • AI3-19015
  • ALE
  • AS-13813
  • Adnephrine
  • Adrenaclick
  • Adrenal
  • Adrenalin
  • Adrenalin chloride
  • Adrenalin in Oil
  • Adrenalin-Medihaler
  • Adrenalina
  • Adrenaline (JP15)
  • Adrenaline (JP17)
  • Adrenaline (L-Adrenaline)
  • Adrenaline/Epinephrine
  • Adrenalinum
  • Adrenamine
  • Adrenan
  • Adrenapax
  • Adrenasol
  • Adrenatrate
  • Adrenine
  • Adrenodis
  • Adrenohorma
  • Adrenosan
  • Adrenutol
  • Adrin
  • Adrine
  • Ana-Guard
  • Ana-Kit
  • Anapen
  • Antiasthmatique
  • Asmatane Mist
  • Asthma meter mist
  • Asthma-nefrin
  • Asthmahaler Mist
  • Asthmanefrin
  • Astmahalin
  • Astminhal
  • Auvi-Q auto-injector
  • Auvi-q
  • BCP09042
  • BDBM44818
  • BDBM50029050
  • BENZYL ALCOHOL, 3,4-DIHYDROXY-.ALPHA.-((METHYLAMINO)METHYL)-, (-)-
  • BIDD:GT0119
  • Balmadren
  • Benzyl alcohol, 3,4-dihydroxy-.alpha.-[(methylamino)methyl]-, (-)-
  • Benzyl alcohol, 3,4-dihydroxy-alpha-((methylamino)methyl)-, (-)-
  • Bernarenin
  • Biorenine
  • Bosmin
  • Brevirenin
  • Bronkaid
  • Bronkaid Mist
  • Bronkaid Suspension Mist
  • Bupivacaine Hcl and Epinephrine
  • C00788
  • CCG-204593
  • CCRIS 4812
  • Citanest Forte
  • Corisol
  • Chelafrin
  • D-Epifrin
  • D-Epinephrine
  • D00095
  • D29A657
  • D88222
  • DB00668
  • DSSTox_CID_2986
  • DSSTox_GSID_22986
  • DSSTox_RID_76819
  • Drenamist
  • Dylephrin
  • Dyspne-Inhal
  • E4250_SIGMA
  • EPI E Z PEN JR
  • EPINEPHRINE COMPONENT OF IONTOCAINE
  • EPINEPHRINE COMPONENT OF LIDOSITE TOPICAL SYSTEM KIT
  • EPINEPHRINE COMPONENT OF OCTOCAINE
  • EPIPEN E Z PEN
  • EPIPEN JR
  • Epi EZ Pen Jr
  • Epifrin
  • Epiglaufrin
  • Epinefrin
  • Epinefrina
  • Epinephran
  • Epinephrin
  • Epinephrine
  • Epinephrine (USP/INN)
  • Epinephrinum
  • Epipen
  • Epipen Auto-Injector
  • Epipen EZ Pen
  • Epipen Jr.
  • Epipen Jr. Auto-Injector
  • Epirenan
  • Epirenin
  • Epitrate
  • Eppy
  • Esphygmogenina
  • Exadri
  • Exadrin
  • GTPL479
  • Glaucon
  • Glaucosan
  • Glauposine
  • Glycirenan
  • HMS3884H06
  • HSCI1_000215
  • HSDB 4289
  • HY-B0447B
  • Haemostasin
  • Haemostatin
  • Hektalin
  • Hemisine
  • Hemostasin
  • Hemostatin
  • Hypernephrin
  • Hyporenin
  • IONTOCAINE COMPONENT EPINEPHRINE
  • IOP
  • Intranefrin
  • Isoptoepinal
  • Kidoline
  • L(-)-Epinephrine
  • L-Adrenaline (Epinephrine)
  • L-Adrenaline Base
  • L-Epinehphrine
  • L-epinephrine
  • LIDOSITE TOPICAL SYSTEM KIT COMPONENT EPINEPHRINE
  • Levo-Methylaminoethanolcatechol
  • Levoepinephrine
  • Levorenen
  • Levorenin
  • Levorenine
  • Levoreninum
  • Lopac-E-4642
  • Lyodrin
  • Lyophrin
  • Metanephrin
  • Methylaminoethanolcatechol
  • Methylarterenol
  • Micronefrin
  • Mucidrina
  • Myosthenine
  • Mytrate
  • NCGC00015417-01
  • NCGC00142615-01
  • NCGC00142615-03
  • NCGC00142615-04
  • NCGC00142615-05
  • NCGC00142615-06
  • NCGC00142615-07
  • NCGC00142615-08
  • NCGC00142615-09
  • NCGC00142615-18
  • NSC 62786
  • NSC-62786
  • NSC62786
  • Nephridine
  • Nieraline
  • OCTOCAINE COMPONENT EPINEPHRINE
  • PDSP1_001120
  • PDSP2_001104
  • Paranephrin
  • Primatene Mist
  • Q-200601
  • Q132621
  • R-(-)-Epinephrine
  • R-Adrenaline
  • Racepinefrine, (r)-
  • Rcra waste number P042
  • Renagladin
  • Renaglandin
  • Renaglandulin
  • Renaleptine
  • Renalina
  • Renoform
  • Renostypricin
  • Renostypticin
  • Renostyptin
  • SDCCGSBI-0050486.P002
  • SMP1_000227
  • SR-01000075267-8
  • SUS-PHRINE SULFITE-FREE
  • SW219274-1
  • Scurenaline
  • Simplene
  • Sindrenina
  • Soladren
  • Sphygmogenin
  • Stryptirenal
  • Styptirenal
  • Supracapsulin
  • Supradin
  • Supranefran
  • Supranephrane
  • Supranephrine
  • Supranol
  • Suprarenaline
  • Suprarenin
  • Suprel
  • Surenine
  • Surrenine
  • Sus-Phrine
  • Sus-phrine sulphite-free
  • Susphrine
  • Symjepi
  • Sympathin I
  • Takamina
  • Takamine
  • Tokamina
  • Tonogen
  • Twinject
  • Twinject 0.15
  • Twinject 0.3
  • Twinject 0.30
  • Vaponefrin
  • Vasoconstrictine
  • Vasoconstrictor
  • Vasodrine
  • Vasoton
  • Vasotonin
  • YKH834O4BH
  • Z2686405805
  • adrenaline
  • bmse000316
  • cid_6852374
  • d-Adrenaline
  • epinephrine
  • l-1-(3,4-Dihydroxyphenyl)-2-methylaminoethanol
  • l-Adrenalin
  • l-Adrenaline
  • l-Epinephine
  • l-Epinephrine (synthetic)
  • l-Epirenamine
  • l-Methylaminoethanolcatechol
  • nchembio747-comp9
  • s2522

Reference codes for other databases

There exist several different chemical codes commonly used in orded to identify molecules:
  • ZINC39089
  • CAS-51-43-4
  • UNII-YKH834O4BH
  • AKOS024283500
  • DTXSID5022986
  • CHEMBL679
  • CHEBI:28918
  • Tox21_111562
  • Tox21_111562_1
  • EINECS 200-098-7
  • SCHEMBL3814

Physico-Chemical properties

IUPAC name4-[(1R)-1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol
Molecular formulaC35H36ClNO3S
Molecular weight586.183
Melting point (ºC)
Boiling point (ºC)
Density (g/cm3)
Molar refractivity172.65
LogP8.9
Topological polar surface area95.7

LogP and topological polar surface area (TPSA) values were estimated using Open Babel software.

The n-octanol/water partition coeficient (Kow) data is applied in toxicology and drug research. Kow values are used, to guess the environmental fate of persistent organic pollutants. High partition coefficients values, tend to accumulate in the fatty tissue of organisms. Molecules with a log(Kow) (or LogP) greater than 5 are considered to bioaccumulate.

TPSA values are the sum of the surface area over all polar atoms or molecules, mainly oxygen and nitrogen, also including hydrogen atoms.

In medicinal chemistry, TPSA is used to assess the ability of a drug to permeabilise cells.

For molecules to penetrate the blood-brain barrier (and act on receptors in the central nervous system), TPSA values below 90 Å2 are required. Thus, molecules with a polar surface area greater than 140 Å2 tend to be poorly permeable to cell membranes.