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In 1 Enoch, sleepless angels praise God with cries of holiness and blessing. In 3 Enoch, the same paired cries come from separate groups of angels, arranging their praise as an exchange between heavenly choirs.
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2500 BCE
1000+ CE

1 Enoch 39:12

Pseudepigrapha, Apocalypses
11 Before Him there is no ceasing. He knows, before the world was created, what is forever and what will be from generation to generation. 12 Those who never sleep bless You; they stand before Your glory and bless and praise and exalt You, saying: "Holy, holy, holy is the Lord of Spirits; He fills the earth with spirits."' 13 Here my eyes saw all those who never sleep; they stand before Him and bless and say: 'You are blessed, and blessed be the name of the Lord forever and ever.' 14 Then my face was changed, for I could no longer look on it.
Date: 200-50 B.C.E. (based on scholarly estimates)

3 Enoch 39:1

Hebrew Book of Enoch
Pseudepigrapha, Apocalypses
R. Ishmael said: Metatron, the Angel, the Prince of the Presence, said to me: When the ministering angels utter the "Holy" then all the explicit names that are graven with a flaming style on the Throne of Glory fly off like eagles, with sixteen wings. And they surround and compass the Holy One, blessed be He, on the four sides of the place of His Shekina. And the angels of the host, and the flaming Servants, and the mighty 'Ophannim, and the Kerubim of the Shekina, and the Holy Chayyoth, and the Seraphim, and the 'Er'ellim, and the Taphsarim and the troops of consuming fire, and the fiery armies, and the flaming hosts, and the holy princes, adorned with crowns, clad in kingly majesty, wrapped in glory, dressed in loftiness, fall upon their faces three times, saying: "Blessed be the name of His glorious kingdom for ever and ever".
Date: 400-600 C.E. (based on scholarly estimates)
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Notes and References

#7607
“... Probably the oldest version of the Qedushah is found at 1 Enoch 39.12–14 (first century AD): Those who do not slumber but stand before your glory, did bless you. They shall bless, praise and extol (you), saying, “Holy, Holy, Holy, Lord of the Spirits; the spirits fill the earth.” And at that place (under his wings) my eyes saw others who stood before him sleepless (and) blessed (him), saying, “Blessed are you and blessed is the name of the Lord of the Spirits forever and ever.” Note that this passage exhibits the same “Holy” + “Blessed” structure as 3 Enoch 39. The expression “Lord of Spirits” is characteristic of the Similitudes of Enoch. It seems likely that this passage, together with 3 Enoch 39 and the prayer in ma‘aseh merkabah, offers evidence for the existence of a type of Qedushah which has not survived in liturgical use, in parallel to Isa 6.3 + Ezek 3.12.31 A Qedushah combining Isa 6.3 and the Temple response “Blessed be the name of his glorious kingdom for ever and ever” (3 Enoch 39) suggests the fusion of li- turgical traditions. ...”

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