From Wikipedia, the free encyclopedia
Semicarbazide
Names
IUPAC name
Identifiers
ChEBI
ChEMBL
ChemSpider
ECHA InfoCard
100.000.308
KEGG
UNII
InChI=1S/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)
Y Key: DUIOPKIIICUYRZ-UHFFFAOYSA-N
Y InChI=1/CH5N3O/c2-1(5)4-3/h3H2,(H3,2,4,5)
Key: DUIOPKIIICUYRZ-UHFFFAOYAJ
Properties
H2 NNHC(=O)NH2
Molar mass
75.08 g/mol
Melting point
96 °C
Hazards
GHS labelling :
Danger
H301 ,
H315 ,
H319 ,
H335
P261 ,
P264 ,
P270 ,
P271 ,
P280 ,
P301+P310 ,
P302+P352 ,
P304+P340 ,
P305+P351+P338 ,
P312 ,
P330 ,
P332+P313 ,
P337+P313 ,
P362 ,
P403+P233 ,
P405
NFPA 704 (fire diamond)
Safety data sheet (SDS)
[1]
Except where otherwise noted, data are given for materials in their
standard state (at 25 °C [77 °F], 100 kPa).
Chemical compound
Semicarbazide is the chemical compound with the formula OC(NH2 )(N2 H3 ). It is a water-soluble white solid. It is a derivative of
urea .
Synthesis
The compound prepared by treating
urea with
hydrazine :
[2]
OC(NH2 )2 + N2 H4 → OC(NH2 )(N2 H3 ) + NH3
A further reaction can occur to give
carbohydrazide :
OC(NH2 )(N2 H3 ) + N2 H4 → OC(N2 H3 )2 + NH3
Derivatives
Semicarbazide is frequently reacted with
aldehydes and
ketones to produce
semicarbazones via a
condensation reaction . This is an example of
imine formation resulting from the reaction of a primary amine with a
carbonyl group . The reaction is useful because semicarbazones, like
oximes and
2,4-DNPs , typically have high melting points and
crystallize , facilitating purification or identification of reaction products.
[3]
Properties
Semicarbazide products (semicarbazones and thiosemicarbazones) are known to have an activity of
antiviral ,
antiinfective and
antineoplastic through binding to
copper or
iron in cells.
Uses, occurrence, detection
Semicarbazide is used in preparing
pharmaceuticals including
nitrofuran
antibacterials (
furazolidone ,
nitrofurazone ,
nitrofurantoin ) and related compounds. It is also a product of degradations of the blowing agent
azodicarbonamide (ADC). Semicarbazide forms in heat-treated flour containing ADC as well as breads made from ADC-treated flour.
[4]
[5]
Semicarbazide is used as a detection reagent in
thin layer chromatography (TLC). Semicarbazide stains α-keto acids on the TLC plate, which can then be viewed under
ultraviolet light.
See also
References
^
CID 5196 from
PubChem
^ Jean-Pierre Schirmann, Paul Bourdauducq "Hydrazine" in Ullmann's Encyclopedia of Industrial Chemistry, Wiley-VCH, Weinheim, 2002.
doi :
10.1002/14356007.a13_177 .
^ John McMurry (1984). Organic Chemistry . Brooks/Cole. p. 676.
^ Becalski, Adam; Lau, Benjamin; Lewis, David; Seaman, Stephen (2004). "Semicarbazide Formation in Azodicarbonamide-Treated Flour: A Model Study". J. Agric. Food Chem . 52 (18): 5730–4.
doi :
10.1021/jf0495385 .
PMID
15373416 .
^ Maria Beatriz de la Calle; Elke Anklam (2005). "Semicarbazide: occurrence in food products and state-of-the-art in analytical methods used for its determination". Anal. Bioanal. Chem . 382 (4): 968–977.
doi :
10.1007/s00216-005-3243-z .
PMID
15947918 .
S2CID
10765283 .
External links
Ionotropic
GABAA Tooltip γ-Aminobutyric acid A receptor
Positive modulators (abridged; see
here for a full list):
α-EMTBL
Alcohols (e.g.,
drinking alcohol ,
2M2B )
Anabolic steroids
Avermectins (e.g.,
ivermectin )
Barbiturates (e.g.,
phenobarbital )
Benzodiazepines (e.g.,
diazepam )
Bromide compounds (e.g.,
potassium bromide )
Carbamates (e.g.,
meprobamate )
Carbamazepine
Chloralose
Chlormezanone
Clomethiazole
Dihydroergolines (e.g.,
ergoloid (dihydroergotoxine) )
Etazepine
Etifoxine
Fenamates (e.g.,
mefenamic acid )
Flavonoids (e.g.,
apigenin ,
hispidulin )
Fluoxetine
Flupirtine
Imidazoles (e.g.,
etomidate )
Kava constituents (e.g.,
kavain )
Lanthanum
Loreclezole
Monastrol
Neuroactive steroids (e.g.,
allopregnanolone ,
cholesterol ,
THDOC )
Niacin
Niacinamide
Nonbenzodiazepines (e.g.,
β-carbolines (e.g.,
abecarnil ),
cyclopyrrolones (e.g.,
zopiclone ),
imidazopyridines (e.g.,
zolpidem ),
pyrazolopyrimidines (e.g.,
zaleplon ))
Norfluoxetine
Petrichloral
Phenols (e.g.,
propofol )
Phenytoin
Piperidinediones (e.g.,
glutethimide )
Propanidid
Pyrazolopyridines (e.g.,
etazolate )
Quinazolinones (e.g.,
methaqualone )
Retigabine (ezogabine)
ROD-188
Skullcap constituents (e.g.,
baicalin )
Stiripentol
Sulfonylalkanes (e.g.,
sulfonmethane (sulfonal) )
Topiramate
Valerian constituents (e.g.,
valerenic acid )
Volatiles /
gases (e.g.,
chloral hydrate ,
chloroform ,
diethyl ether ,
paraldehyde ,
sevoflurane )
Negative modulators:
1,3M1B
3M2B
11-Ketoprogesterone
17-Phenylandrostenol
α3IA
α5IA (LS-193,268)
β-CCB
β-CCE
β-CCM
β-CCP
β-EMGBL
Anabolic steroids
Amiloride
Anisatin
β-Lactams (e.g.,
penicillins ,
cephalosporins ,
carbapenems )
Basmisanil
Bemegride
Bicyclic phosphates (
TBPS ,
TBPO ,
IPTBO )
BIDN
Bilobalide
Bupropion
CHEB
Chlorophenylsilatrane
Cicutoxin
Cloflubicyne
Cyclothiazide
DHEA
DHEA-S
Dieldrin
(+)-DMBB
DMCM
DMPC
EBOB
Etbicyphat
FG-7142 (ZK-31906)
Fiproles (e.g.,
fipronil )
Flavonoids (e.g.,
amentoflavone ,
oroxylin A )
Flumazenil
Fluoroquinolones (e.g.,
ciprofloxacin )
Flurothyl
Furosemide
Golexanolone
Iomazenil (123 I)
IPTBO
Isopregnanolone (sepranolone)
L-655,708
Laudanosine
Lindane
MaxiPost
Morphine
Morphine-3-glucuronide
MRK-016
Naloxone
Naltrexone
Nicardipine
Nonsteroidal antiandrogens (e.g.,
apalutamide ,
bicalutamide ,
enzalutamide ,
flutamide ,
nilutamide )
Oenanthotoxin
Pentylenetetrazol (pentetrazol)
Phenylsilatrane
Picrotoxin (i.e.,
picrotin ,
picrotoxinin and
dihydropicrotoxinin )
Pregnenolone sulfate
Propybicyphat
PWZ-029
Radequinil
Ro 15-4513
Ro 19-4603
RO4882224
RO4938581
Sarmazenil
SCS
Suritozole
TB-21007
TBOB
TBPS
TCS-1105
Terbequinil
TETS
Thujone
U-93631
Zinc
ZK-93426
GABAA -ρ Tooltip γ-Aminobutyric acid A-rho receptor
Metabotropic
GABAB Tooltip γ-Aminobutyric acid B receptor