Home > Compound List > Compound details
54-49-9 molecular structure
click picture or here to close

3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol

ChemBase ID: 492
Molecular Formular: C9H13NO2
Molecular Mass: 167.20502
Monoisotopic Mass: 167.09462866
SMILES and InChIs

SMILES:
O[C@@H]([C@@H](N)C)c1cc(O)ccc1
Canonical SMILES:
C[C@@H]([C@@H](c1cccc(c1)O)O)N
InChI:
InChI=1S/C9H13NO2/c1-6(10)9(12)7-3-2-4-8(11)5-7/h2-6,9,11-12H,10H2,1H3/t6-,9-/m0/s1
InChIKey:
WXFIGDLSSYIKKV-RCOVLWMOSA-N

Cite this record

CBID:492 http://www.chembase.cn/molecule-492.html

Collapse All Expand All

NAMES AND DATABASE IDS

NAMES AND DATABASE IDS

Names Database IDs
IUPAC name
3-[(1R,2S)-2-amino-1-hydroxypropyl]phenol
IUPAC Traditional name
metaraminol
Brand Name
Aramine
Icoral B
Metaradrine
Pressonex
Pressorol
Synonyms
Metaraminolum [Latin]
Metaraminolum [INN-Latin]
Metaraminol Bitartrate
M-Hydroxypropadrine
M-Hydroxyphenylpropanolamine
M-Hydroxy Norephedrine
L-Metaraminol
Hydroxynorephedrine
Metaraminol
CAS Number
54-49-9
PubChem SID
160963955
46505593
PubChem CID
5906

DATA SOURCES

DATA SOURCES

All Sources Commercial Sources Non-commercial Sources
Data Source Data ID
DrugBank DB00610 external link
PubChem 5906 external link
Data Source Data ID Price

CALCULATED PROPERTIES

CALCULATED PROPERTIES

JChem ALOGPS 2.1
Acid pKa 9.031579  H Acceptors
H Donor LogD (pH = 5.5) -2.383171 
LogD (pH = 7.4) -1.2987354  Log P -0.045079757 
Molar Refractivity 46.8936 cm3 Polarizability 18.594221 Å3
Polar Surface Area 66.48 Å2 Rotatable Bonds
Lipinski's Rule of Five true 
Log P -0.59  LOG S -1.12 
Solubility (Water) 1.28e+01 g/l 

PROPERTIES

PROPERTIES

Physical Property Bioassay(PubChem)
Solubility
1000 g/L expand Show data source
Hydrophobicity(logP)
0.6 expand Show data source

DETAILS

DETAILS

DrugBank DrugBank
DrugBank - DB00610 external link
Item Information
Drug Groups approved
Description An adrenergic agonist that acts predominantly at alpha adrenergic receptors and also stimulates the release of norepinephrine. It has been used primarily as a vasoconstrictor in the treatment of hypotension. [PubChem]
Indication For the treatment and prevention of hypotension due to hemorrhage, spinal anesthesia, and shock associated with brain damage
Pharmacology Metaraminol is a potent sympathomimetic amine that increases both systolic and diastolic blood pressure. Metaraminol is indicated for prevention and treatment of the acute hypotensive state occurring with spinal anesthesia. It is also indicated as adjunctive treatment of hypotension due to hemorrhage, reactions to medications, surgical complications, and shock associated with brain damage due to trauma or tumor. Metaraminol acts on both α1-adrenergic receptors but appears to have no effect on β-adrenergic receptors. It acts by increasing the force of the heart's pumping action as well as constricting peripheral blood vessels.
Toxicity LD50=240 mg/kg (rat, oral); LD50=99 mg/kg (mouse, oral)
Affected Organisms
Humans and other mammals
Biotransformation Hepatic
Absorption The effect starts 1-2 min after IV injection, 10 min after IM injection, 5-20 min after subcutaneous injection.
Protein Binding Approximately 45%
References
McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. [Pubmed]
Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. [Pubmed]
Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] Urologe A. 1988 Jul;27(4):225-9. [Pubmed]
External Links
Wikipedia
RxList

REFERENCES

REFERENCES

From Suppliers Google Scholar IconGoogle Scholar PubMed iconPubMed Google Books IconGoogle Books
  • • McDonald M, Santucci RA: Successful management of stuttering priapism using home self-injections of the alpha-agonist metaraminol. Int Braz J Urol. 2004 Mar-Apr;30(2):121-2. Pubmed
  • • Koga S, Shiraishi K, Saito Y: Post-traumatic priapism treated with metaraminol bitartrate: case report. J Trauma. 1990 Dec;30(12):1591-3. Pubmed
  • • Block T, Sturm W, Ernst G, Staehler G, Schmiedt E: [Metaraminol in therapy of various forms of priapism] Urologe A. 1988 Jul;27(4):225-9. Pubmed
  • Searching...Please wait...

PATENTS

PATENTS

PubChem iconPubChem Patent Google Patent Search IconGoogle Patent

INTERNET

INTERNET

Baidu iconBaidu google iconGoogle