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3 0305 - Thuốc giảm đau, gây nghiện
3 0305 - Thuốc giảm đau, gây nghiện
Do hoaøn caûnh
Do tö töôûng
❑ Gaây nghieän
MORPHIN
Chieát töø nhöïa caây Papaver somniferum
OCH3
R'O
OCH3
Phenanthren (morphin)
Benzylquinolein (Papaverin)
CH3
CAÙC DAÃN CHAÁT TOÅNG HÔÏP TÖØ MORPHIN
N
R'
R"
RO O
Teân chaát R R’ R” Coâng duïng
H OH
Codein CH3 H Nhö treân Giaûm ñau, öùc cheá phaûn xaï
ho
CH3 O
OH phenol HO 3
1
N baäc 3
11
Caàu noái ether O 9
N CH3
15
16
6
OH alcool HO
Noái ñoâi
11
Taùc duïng raát maïnh (fentanyl….) O 9
N CH3
15
Gaây nghieän maïnh
16
6
HO
R1 R3 N CH3
C
R2 R4 CH3
H3C O
N
CH2 OC2H5
O2N N
CH2CH2N(C2H5)2 Etonitazen
5 10 15
H-Glu-Leu-Thr-Gly-Gln-Arg-Leu-Arg-Gln-Gly-Asp-Pro-Asn-Ala
30
Leu-Ser-His-Glu-Leu-Ala-Asn-Pro-Gly-Glu-Gly-Asp-Asn-Ala-Gly
45
Leu-Ala-Asp-Leu-Val-Ala-Ala-Glu-Lys-Lys-Asp-Glu-Gly-Pro-Tyr
60
Arg-Lys-Asp-Lys-Pro-Pro-Ser-Gly-Trp-Asg-Phe-His-Glu-Met-Arg
61
Tyr
Methionin
Enkephalin
Gly-Gly
65
Met-Phe
70
Thr-Ser-Glu-Lys-Ser
Val-Leu-Pro-Thr-Gla ß - Endorphin
80
Thr-Leu-Phe-Lys-Asn
85
Asn-Lys-Ile-Ile-Ala
91
Caùc endorphin
Ala-Tyr-Lys-Lys-Gly-Glu-OH
HO MORPHIN HYDROCLORID
HO HO OH
K3[Fe(CN)6]/HCl
O O O + H4[Fe(CN)6]
N CH3 N CH3 H3C N
HO HO OH
HO HO HO
O O O
_ H2O To
N CH3 N CH3 N CH3
+
H
HO
HO HO
HO HO
N CH3 N CH3
Taïo saûn phaåm azo hoaù (do OH phenol)
HO N N SO3H
O
H N CH3
HO H
H
▪ PP trung hoaø
Thaän troïng
O
Chieát töø nhöïa opium
N CH3 .H3PO4
HO H3CO
H3C N CH3 Cl
O O
CH3
N CH3 + CH3OH N CH3
KOH
HO HO
Khoâng cho phaûn öùng cuûa OH phenol
UV max ôû 284 nm
CH3COO
RO
R = H Dihydromorphinon
O (Dilaudid)
N CH3
Giaûm ñau
O
Trò ho
CAÙC DC HYDROGEN HOAÙ 7-8, THEÂM OH ÔÛ C14
RO
R = H (Oxymorphon)
OH
O R = CH3 (Oxycodon)
N CH3
HO
O
Cl
CH2 Cl2
O OH + O
O OH
NH O
Cyclobutan carbonyl clorid N
O
14-hydroxydihydro- O O
normorphinon HO
LiAlH4 / THF
O OH
N
HO
Nalbuphin
Meperidin
H3C N
COOC2H5
O
O
N CH3
CH3
O
N
Alfentanyl
H3C
O N
O
CH3
Fentanyl N O
O
Remifentanyl N CH3
O
O
CH3
H3C
O H3C
O N CH3
H3C N
N CH3
S
H3C O
Sufentanyl Methadon
CH3 O
N CH3
O CH3
N
N H3C CH3
O
O
Dextromoramid
Dextropropoxyphen
HO HO
N CH2
N CH3 OH
H
Levorphanol Butorphanol
HO
Buprenorphin
H N
H3C
O H
H3C OH
H3C CH3
CH3
H3C H CH3
HO NH2
N CH3
HO CH3
H
H
Dezorcin Pentazorcin
CAÙC CHAÁT COÙ TD ÑOÁI KHAÙNG MORPHIN
HO
Nalorphin (N-allylmorphin)
O HO
H N
H
HO CH2
N
H
HO
CH2
Levallorphan
O
H N
OH
O CH2 Naloxon
HO
Naltrexon
O
H N
OH
O
HO
O
Nalmefen
H N
OH
H2C
CAÙC CHAÁT COÙ TD TRÒ HO
H3C
O
Dextromethorphan
SD raát nhieàu
O O CH2(CH2OCH2)9H
Benzonatat
HO C6H5 O
N CH2 CH2 C C N
CH3 Loperamid
(Imodium®)
Cl CH3
C6H5
H5C2OOC C6H5 O
Diphenoxylat
N CH2 CH2 C C CN
C6H5 (Diarsed®)